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Showing 180 of 1,179 sailings
Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Sep 18 – Sep 26, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexBuck Island ReefPrivate Full-Day Boat CharterWalk El Morro & Old San Juan's City Walls +1 more
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from $1,232
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Carnival · Carnival VistaRound-trip
Caribbean 8 nights Sep 19, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Celebration Key, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls27 Charcos of Damajagua +1 more
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from $647
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MSC Cruises · MSC World AmericaRound-trip
Bahamas 7 nights Sep 19 – Sep 26, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari
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from $633
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Royal Caribbean · Allure of the SeasRound-trip
Bahamas 8 nights Sep 19 – Sep 27, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico · Perfect Day at CocoCay · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $668
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Sep 19 – Sep 26, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterJost Van DykeRandom Wind 'Paradise Day Sail' +2 more
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from $557
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Princess · Regal PrincessRound-trip
Caribbean 14 nights Sep 26 – Oct 10, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida · Roatan, Honduras · Belize City, Belize · Cozumel, Mexico · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMaho Beach +3 more
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from $2,768
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Sep 26 – Oct 3, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $606
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Carnival · Carnival CelebrationRound-trip
Caribbean 7 nights Sep 27, 2026 from Miami, Florida
Miami, Florida · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City WallsKayak the Lucayan Caves & Gold Rock Beach with the…
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from $578
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Disney · Disney DreamRound-trip
Bahamas 7 nights Oct 2 – Oct 9, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Castaway Cay, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $1,571
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Carnival · Carnival MagicRound-trip
Bahamas 8 nights Oct 3, 2026 from Miami, Florida
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · … · Miami, Florida6 ports
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Horseback Riding by Land & SeaWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail' +1 more
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from $617
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MSC Cruises · MSC World AmericaRound-trip
Bahamas 7 nights Oct 3 – Oct 10, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari
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from $538
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 3 – Oct 10, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $583
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Princess · Caribbean PrincessRound-trip
Caribbean 7 nights Oct 4 – Oct 11, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexWalk El Morro & Old San Juan's City Walls27 Charcos of DamajaguaGibbs Cay Private Stingray Swim & Reef Snorkel
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from $619
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Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Oct 4 – Oct 11, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Philipsburg, St. Maarten · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'
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from $1,134
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Royal Caribbean · Icon of the SeasRound-trip
Bahamas 7 nights Oct 10 – Oct 17, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterWalk El Morro & Old San Juan's City WallsDaredevil's Peak
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from $892
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 10 – Oct 17, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $606
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Cunard · Queen ElizabethRound-trip
Caribbean 21 nights Oct 15 – Nov 5, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida13 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida · Grand Turk, Turks and Caicos · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsAdventure AntiguaGros Piton Summit Hike +7 more
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from $1,898
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Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Oct 16 – Oct 24, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexBuck Island ReefPrivate Full-Day Boat CharterWalk El Morro & Old San Juan's City Walls +1 more
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from $1,592
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Viking Ocean · Viking SeaRepositioning
Caribbean 20 nights Oct 16 – Nov 5, 2026 from Civitavecchia (Rome), Italy to San Juan, Puerto Rico
Civitavecchia (Rome), Italy · Florence, Italy · … · San Juan, Puerto Rico13 ports
Civitavecchia (Rome), Italy · Florence, Italy · Monte Carlo, Monaco · Marseille, France · Sete, France · Barcelona, Spain · Valencia, Spain · Sail the Alboran Sea · Sail the Atlantic Ocean · Funchal, Madeira, Portugal · Sail the Atlantic Ocean · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayUffizi GalleryCasino de Monte-CarloCalanques National Park Boat Cruise from the Old P… +6 more
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from $7,398
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Carnival · Carnival DreamRound-trip
Caribbean 14 nights Oct 17, 2026 from Galveston, Texas
Galveston, Texas · Key West, Florida · … · Galveston, Texas10 ports
Galveston, Texas · Key West, Florida · Grand Turk, Turks and Caicos · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Ocho Rios, Jamaica · Galveston, Texas
★ Bucket-list Moody GardensDry Tortugas National ParkGibbs Cay Private Stingray Swim & Reef SnorkelWalk El Morro & Old San Juan's City Walls +5 more
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from $1,110
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Carnival · Carnival VistaRound-trip
Caribbean 8 nights Oct 17, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Celebration Key, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls27 Charcos of Damajagua +1 more
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from $707
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Disney · Disney DestinyRound-trip
Bahamas 7 nights Oct 17 – Oct 24, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · Castaway Cay, Bahamas · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraAbaco Backcountry Fishing AdventureWalk El Morro & Old San Juan's City Walls +1 more
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from $1,893
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MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Oct 17 – Oct 31, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,448
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 17 – Oct 24, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterJost Van DykeRandom Wind 'Paradise Day Sail' +2 more
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from $767
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Carnival · Carnival VeneziaRound-trip
Caribbean 14 nights Oct 18, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · Antigua, Antigua & Barbuda · Fort-de-France, Martinique · Grenada, Caribbean · Kingstown, St. Vincent (dock) · Bridgetown, Barbados · Philipsburg, St. Maarten · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Adventure AntiguaMount Pelée & Saint-Pierre +4 more
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from $994
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Virgin · Valiant LadyOne-way
Bermuda 12 nights Oct 19, 2026 from Brooklyn, NY to San Juan, Puerto Rico
Brooklyn, NY · Kings Wharf, Bermuda · … · San Juan, Puerto Rico7 ports
Brooklyn, NY · Kings Wharf, Bermuda · Bimini, Bahamas · St. Croix, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list NYC Private VIP Tour by VehicleDolphin QuestSwim with Wild Dolphins at Honeymoon HarbourBuck Island Reef +3 more
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from $1,188
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Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Oct 22 – Nov 1, 2026 from Baltimore, Maryland to San Juan, Puerto Rico
Baltimore, Maryland · Grand Turk, Turks and Caicos · … · San Juan, Puerto Rico8 ports
Baltimore, Maryland · Grand Turk, Turks and Caicos · Philipsburg, St. Maarten · Roseau, Dominica · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list National AquariumGibbs Cay Private Stingray Swim & Reef SnorkelRandom Wind 'Paradise Day Sail'Boiling Lake Hike +4 more
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from $1,212
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Viking Ocean · Viking SeaRepositioning
Caribbean 13 nights Oct 23 – Nov 5, 2026 from Barcelona, Spain to San Juan, Puerto Rico
Barcelona, Spain · Valencia, Spain · … · San Juan, Puerto Rico8 ports
Barcelona, Spain · Valencia, Spain · Sail the Alboran Sea · Sail the Atlantic Ocean · Funchal, Madeira, Portugal · Sail the Atlantic Ocean · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Sagrada FamiliaOceanograficPico do Arieiro to Pico RuivoRandom Wind 'Paradise Day Sail' +1 more
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from $3,299
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Norwegian · Norwegian SunOne-way
Bermuda 13 nights Oct 24 – Nov 6, 2026 from New York, New York to Miami, Florida
New York, New York · Royal Naval Dockyard, Bermuda · … · Miami, Florida10 ports
New York, New York · Royal Naval Dockyard, Bermuda · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cabo Rojo, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +6 more
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from $1,219
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 24 – Oct 31, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $579
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 14 nights Oct 25, 2026 from Miami, Florida
Miami, Florida · Saint John/cruz Bay · … · Miami, Florida11 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Road Bay, Anguilla · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelRandom Wind 'Paradise Day Sail' +5 more
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from $12,280
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MSC Cruises · MSC GrandiosaRepositioning
Mediterranean 19 nights Oct 25 – Nov 13, 2026 from Marseille, France to Miami, Florida
Marseille, France · Genoa, Italy · … · Miami, Florida9 ports
Marseille, France · Genoa, Italy · La Spezia (Cinque Terre), Italy · Civitavecchia (Rome), Italy · Palma de Mallorca, Spain · Barcelona, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Calanques National Park Boat Cruise from the Old P…Sail straight to Portofino from the cruise dockPrivate Cinque Terre by Minivan & Ferryboat from L…Vatican, Sistine Chapel & Colosseum in One Day +5 more
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from $1,499
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Royal Caribbean · Allure of the SeasRound-trip
Caribbean 7 nights Oct 25 – Nov 1, 2026 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida6 ports
Miami, Florida · Nassau, Bahamas · Perfect Day at CocoCay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma PigsDaredevil's PeakWalk El Morro & Old San Juan's City Walls +1 more
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from $769
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Royal Caribbean · Oasis of the SeasRound-trip
Bahamas 9 nights Oct 25 – Nov 3, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Port Canaveral, Florida · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Port Canaveral, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandKennedy Space Center Visitor ComplexDaredevil's PeakWalk El Morro & Old San Juan's City Walls +1 more
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from $1,256
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Royal Caribbean · Star of the SeasRound-trip
Bahamas 7 nights Oct 25 – Nov 1, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Philipsburg, St. Maarten · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexDaredevil's PeakWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'
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from $1,234
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MSC Cruises · MSC GrandiosaOne-way
Caribbean 18 nights Oct 26 – Nov 13, 2026 from Genoa, Italy to Miami, Florida
Genoa, Italy · La Spezia (Cinque Terre), Italy · … · Miami, Florida8 ports
Genoa, Italy · La Spezia (Cinque Terre), Italy · Civitavecchia (Rome), Italy · Palma de Mallorca, Spain · Barcelona, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Sail straight to Portofino from the cruise dockPrivate Cinque Terre by Minivan & Ferryboat from L…Vatican, Sistine Chapel & Colosseum in One DayLa Seu Cathedral + Rooftop Terraces Climb +4 more
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from $1,027
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Cunard · Queen ElizabethRound-trip
Caribbean 21 nights Oct 27 – Nov 17, 2026 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida13 ports
Miami, Florida · Grand Turk, Turks and Caicos · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +7 more
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from $1,658
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MSC Cruises · MSC GrandiosaRepositioning
Mediterranean 17 nights Oct 28 – Nov 14, 2026 from Civitavecchia (Rome), Italy to Port Canaveral, Florida
Civitavecchia (Rome), Italy · Palma de Mallorca, Spain · … · Port Canaveral, Florida7 ports
Civitavecchia (Rome), Italy · Palma de Mallorca, Spain · Barcelona, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Miami, Florida · Port Canaveral, Florida
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayLa Seu Cathedral + Rooftop Terraces ClimbSagrada FamiliaPico do Arieiro to Pico Ruivo +3 more
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from $1,424
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Windstar · Star PrideRound-trip
Caribbean 11 nights Oct 28 – Nov 8, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Falmouth Harbour, Antigua · Les Saintes, Guadeloupe · Rodney Bay, St. Lucia · St. Georges, Grenada, West Indies · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +6 more
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from $3,930
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Azamara · Azamara JourneyOne-way
Bermuda 9 nights Oct 29 – Nov 7, 2026 from New York, New York to San Juan, Puerto Rico
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourRising Son CatamaranRandom Wind 'Paradise Day Sail'Norman Island +1 more
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from $3,719
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Princess · Coral PrincessRound-trip
Bahamas 10 nights Oct 29 – Nov 8, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Princess Cays, Bahamas · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Princess Cays, Bahamas · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Bungalow Day27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls +3 more
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from $834
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MSC Cruises · MSC GrandiosaRepositioning
Mediterranean 15 nights Oct 30 – Nov 14, 2026 from Palma de Mallorca, Spain to Port Canaveral, Florida
Palma de Mallorca, Spain · Barcelona, Spain · … · Port Canaveral, Florida6 ports
Palma de Mallorca, Spain · Barcelona, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Miami, Florida · Port Canaveral, Florida
★ Bucket-list La Seu Cathedral + Rooftop Terraces ClimbSagrada FamiliaPico do Arieiro to Pico RuivoWalk El Morro & Old San Juan's City Walls +2 more
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from $740
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Regent · Seven Seas SplendorOne-way
Caribbean 16 nights Oct 30 – Nov 15, 2026 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida14 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Willis Island · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · San Juan, Puerto Rico · Willis Island · Miami, Florida
★ Bucket-list Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Zodiac Circumnavigation of Willis IslandBridgeClimb Sydney +7 more
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from $16,099
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Carnival · Carnival MagicRound-trip
Bahamas 8 nights Oct 31, 2026 from Miami, Florida
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · … · Miami, Florida6 ports
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Horseback Riding by Land & SeaWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail' +1 more
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from $557
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MSC Cruises · MSC GrandiosaRepositioning
Mediterranean 14 nights Oct 31 – Nov 14, 2026 from Barcelona, Spain to Port Canaveral, Florida
Barcelona, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Miami, Florida · Port Canaveral, Florida
★ Bucket-list Sagrada FamiliaPico do Arieiro to Pico RuivoWalk El Morro & Old San Juan's City WallsStar Island & Millionaire's Row Skyline Cruise on… +1 more
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from $638
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MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Oct 31 – Nov 14, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,235
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Princess · Regal PrincessRound-trip
Caribbean 8 nights Oct 31 – Nov 8, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachWalk El Morro & Old San Juan's City Walls27 Charcos of Damajagua +1 more
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from $749
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 31 – Nov 7, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $722
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Virgin · Valiant LadyRound-trip
Caribbean 7 nights Oct 31, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Willemstad, Curacao · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Curaçao Island Tour with Local Ex…ArubaMount Pelée & Saint-Pierre +1 more
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from $763
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Carnival · Carnival VeneziaRound-trip
Caribbean 7 nights Nov 1, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Celebration Key, Bahamas · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexKayak the Lucayan Caves & Gold Rock Beach with the…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…
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from $515
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IOne-way
Mediterranean 11 nights Nov 1, 2026 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Cadiz (Seville), Spain · … · Miami, Florida12 ports
Barcelona, Spain · Cadiz (Seville), Spain · Funchal, Madeira, Portugal · St. John's, Antigua · Road Bay, Anguilla · San Juan, Puerto Rico · Miami, Florida · Merida, Mexico · Roatan, Honduras · Belize City, Belize · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Sagrada FamiliaReal Alcázar de SevillaPico do Arieiro to Pico RuivoPrivate Half-Day Island Adventure & Trunk Bay Beach +7 more
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from $11,735
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Explora Journeys · EXPLORA IIIOne-way
Caribbean 14 nights Nov 1, 2026 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · Miami, Florida6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Road Bay, Anguilla · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandMt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +2 more
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from $5,680
Book This Cruise@ Cruisebound
MSC Cruises · MSC PoesiaRound-trip
Caribbean 21 nights Nov 1 – Nov 22, 2026 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · … · Miami, Florida15 ports
Miami, Florida · Ocho Rios, Jamaica · Cartagena, Colombia · Colon, Panama · Puerto Limon, Costa Rica · Roatan, Honduras · Belize City, Belize · Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleThe Roman Theatre of Cartagena with the Rafael Mon…Panama Canal Full Transit +9 more
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from $2,075
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Royal Caribbean · Allure of the SeasRound-trip
Bahamas 7 nights Nov 1 – Nov 8, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Daredevil's PeakWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike
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from $735
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 1 – Nov 8, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $726
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Celebrity · Celebrity ConstellationRepositioning
Mediterranean 15 nights Nov 2 – Nov 17, 2026 from Civitavecchia (Rome), Italy to San Juan, Puerto Rico
Civitavecchia (Rome), Italy · Valencia, Spain · … · San Juan, Puerto Rico7 ports
Civitavecchia (Rome), Italy · Valencia, Spain · Cartagena, Spain · Malaga, Spain · Tangier, Morocco · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayOceanograficThe Roman Theatre of Cartagena with the Rafael Mon…Granada & the Alhambra +3 more
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from $746
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MSC Cruises · MSC GrandiosaRepositioning
Caribbean 10 nights Nov 3 – Nov 13, 2026 from Funchal, Madeira, Portugal to Miami, Florida
Funchal, Madeira, Portugal · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Pico do Arieiro to Pico RuivoWalk El Morro & Old San Juan's City WallsStar Island & Millionaire's Row Skyline Cruise on…
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from $659
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Cunard · Queen ElizabethRound-trip
Caribbean 21 nights Nov 5 – Nov 26, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida14 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsAdventure AntiguaGros Piton Summit Hike +8 more
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from $1,618
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 5 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $5,399
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Azamara · Azamara JourneyOne-way
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +3 more
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from $2,341
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Disney · Disney TreasureRound-trip
Bahamas 7 nights Nov 7 – Nov 14, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Tortola, B.V.I. · San Juan, Puerto Rico · Castaway Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexJost Van DykeWalk El Morro & Old San Juan's City WallsAbaco Backcountry Fishing Adventure
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from $1,840
Book This Cruise@ Cruisebound
Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Nov 7 – Nov 15, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $709
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $684
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 11 nights Nov 7 – Nov 18, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $7,150
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Virgin · Valiant LadyRound-trip
Caribbean 7 nights Nov 7, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,603
Book This Cruise@ Cruisebound
Carnival · Carnival CelebrationRound-trip
Caribbean 7 nights Nov 8, 2026 from Miami, Florida
Miami, Florida · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City WallsKayak the Lucayan Caves & Gold Rock Beach with the…
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from $560
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Nov 8, 2026 from Miami, Florida
Miami, Florida · Providenciales, Turks & Caicos · … · Miami, Florida13 ports
Miami, Florida · Providenciales, Turks & Caicos · Puerto Plata, Dominican Republic · La Romana, Dominican Republic · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefThe full 27 jumps at the Damajagua WaterfallsSaona Island Private Speedboat & Natural Pool Day +6 more
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from $8,735
Book This Cruise@ Cruisebound
Royal Caribbean · Allure of the SeasRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Daredevil's PeakWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter
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from $806
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $549
Book This Cruise@ Cruisebound
Virgin · Resilient LadyRound-trip
Caribbean 8 nights Nov 8, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsNorman Island +1 more
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from $872
Book This Cruise@ Cruisebound
Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $2,411
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 9 – Nov 21, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $979
Book This Cruise@ Cruisebound
Oceania · Oceania InsigniaRepositioning
Mediterranean 15 nights Nov 9 – Nov 24, 2026 from Lisbon, Portugal to Miami, Florida
Lisbon, Portugal · Arrecife, Lanzarote, Canary Islands · … · Miami, Florida7 ports
Lisbon, Portugal · Arrecife, Lanzarote, Canary Islands · Las Palmas, Gran Canaria, Canary Islands · Santa Cruz de La Palma, Spain · San Juan, Puerto Rico · Nassau, Bahamas · Miami, Florida
★ Bucket-list SintraTimanfaya Volcanic ParkRoque Nublo & TejedaTajogaite Volcano +3 more
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from $2,695
Book This Cruise@ Cruisebound
Regent · Seven Seas MarinerRound-trip
Caribbean 22 nights Nov 9 – Dec 1, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida16 ports
Miami, Florida · Willis Island · Bridgetown, Barbados · Port of Spain, Trinidad · Willis Island · Santarem, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Alter do Chao, Brazil · Willis Island · St. Georges, Grenada, West Indies · Willis Island · San Juan, Puerto Rico · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandSwim with wild green sea turtles + two shipwrecks…Caroni Swamp +6 more
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from $17,349
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IOne-way
Caribbean 5 nights Nov 12, 2026 from St. John's, Antigua to Miami, Florida
St. John's, Antigua · Road Bay, Anguilla · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Private Half-Day Island Adventure & Trunk Bay BeachPrivate Island HoppingWalk El Morro & Old San Juan's City WallsStar Island & Millionaire's Row Skyline Cruise on…
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from $3,150
Book This Cruise@ Cruisebound
MSC Cruises · MSC PoesiaRound-trip
Caribbean 21 nights Nov 12 – Dec 3, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida15 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida · Ocho Rios, Jamaica · Cartagena, Colombia · Colon, Panama · Puerto Limon, Costa Rica · Roatan, Honduras · Belize City, Belize · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterPrivate Island TourRandom Wind 'Paradise Day Sail' +9 more
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from $2,055
Book This Cruise@ Cruisebound
Norwegian · Norwegian PrimaOne-way
Caribbean 3 nights Nov 12 – Nov 15, 2026 from Port Canaveral, Florida to San Juan, Puerto Rico
Port Canaveral, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls
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from $429
Book This Cruise@ Cruisebound
Disney · Disney DreamRound-trip
Caribbean 7 nights Nov 13 – Nov 20, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Castaway Cay, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $1,865
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 7 nights Nov 14 – Nov 21, 2026 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +4 more
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from $1,889
Book This Cruise@ Cruisebound
Carnival · Carnival VistaRound-trip
Caribbean 8 nights Nov 14, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Celebration Key, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls27 Charcos of Damajagua +1 more
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from $607
Book This Cruise@ Cruisebound
MSC Cruises · MSC World AmericaRound-trip
Bahamas 7 nights Nov 14 – Nov 21, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari
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from $528
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 14 – Nov 21, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay BeachBoiling Lake Hike +2 more
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from $479
Book This Cruise@ Cruisebound
Virgin · Valiant LadyRound-trip
Caribbean 6 nights Nov 14, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandPrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +1 more
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from $714
Book This Cruise@ Cruisebound
Carnival · Carnival VeneziaRound-trip
Caribbean 7 nights Nov 15, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Celebration Key, Bahamas · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexKayak the Lucayan Caves & Gold Rock Beach with the…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…
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from $504
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Island HoppingPrivate Half-Day Island Adventure & Trunk Bay BeachPrivate Pyramids of Giza, Sphinx & Grand Egyptian… +4 more
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from $10,200
Book This Cruise@ Cruisebound
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachSwim with wild green sea turtles + two shipwrecks… +3 more
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from $859
Book This Cruise@ Cruisebound
Oceania · Oceania MarinaRepositioning
Caribbean 25 nights Nov 15 – Dec 10, 2026 from Civitavecchia (Rome), Italy to Miami, Florida
Civitavecchia (Rome), Italy · Naples, Italy · … · Miami, Florida17 ports
Civitavecchia (Rome), Italy · Naples, Italy · Messina, Sicily, Italy · Valletta, Malta · Trapani, Italy · La Goulette, Tunisia · Cagliari, Sardinia, Italy · Mahon, Minorca, Spain · Palma de Mallorca, Spain · Barcelona, Spain · Valencia, Spain · Alicante, Spain · Malaga, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPompeii with a Licensed ArchaeologistTaormina's Ancient Greek Theatre, framed by Mount…St John's Co-Cathedral & the Caravaggio masterpieces +13 more
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from $10,049
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Princess · Sun PrincessRound-trip
Caribbean 14 nights Nov 15 – Nov 29, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Cozumel, Mexico · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Cozumel, Mexico · Costa Maya, Mexico · Roatan, Honduras · Fort Lauderdale (Port Everglades), Florida · Relaxaway, Half Moon Cay · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowEl Cielo + Palancar + Columbia 3-Stop SnorkelChacchoben Mayan RuinsHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +2 more
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from $1,408
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Royal Caribbean · Independence of the SeasRound-trip
Bahamas 7 nights Nov 15 – Nov 22, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Daredevil's PeakWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter
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from $595
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $548
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 15 – Nov 25, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $4,999
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Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $6,153
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Norwegian · Norwegian GetawayRound-trip
Caribbean 7 nights Nov 16 – Nov 23, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Great Stirrup Cay, Bahamas · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Great Stirrup Cay, Bahamas · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexSilver Cove Private VillaPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls +1 more
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from $499
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 11 nights Nov 17 – Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Fort-de-France, Martinique · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +5 more
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from $7,649
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Cunard · Queen ElizabethRound-trip
Mexico 21 nights Nov 17 – Dec 8, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida14 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarMartha Brae River Bamboo RaftingHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +8 more
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from $2,518
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Oceania · Oceania AlluraRepositioning
Mediterranean 15 nights Nov 17 – Dec 2, 2026 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Malaga, Spain · … · Miami, Florida6 ports
Barcelona, Spain · Malaga, Spain · Agadir, Morocco · Arrecife, Lanzarote, Canary Islands · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Sagrada FamiliaGranada & the AlhambraParadise Valley & Atlas FoothillsTimanfaya Volcanic Park +2 more
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from $3,815
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Silversea · Silver ShadowRound-trip
Caribbean 12 nights Nov 18 – Nov 30, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +4 more
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from $8,550
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Princess · Sky PrincessRound-trip
Caribbean 9 nights Nov 20 – Nov 29, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Grand Turk, Turks and Caicos · … · Port Canaveral, Florida7 ports
Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Celebration Key, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexGibbs Cay Private Stingray Swim & Reef Snorkel27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls +2 more
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from $838
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Seabourn · Seabourn OvationOne-way
Caribbean 15 nights Nov 20 – Dec 5, 2026 from Miami, Florida to Philipsburg, St. Maarten
Miami, Florida · San Juan, Puerto Rico · … · Philipsburg, St. Maarten13 ports
Miami, Florida · San Juan, Puerto Rico · Great Harbor, Peter Island, BVI · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Port Elizabeth, Saint Vincent · Bridgetown, Barbados · Rodney Bay, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Full-Day Sail to The Baths, Virgin GordaMt. Liamuiga Volcano Crater Hike +8 more
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from $6,559
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Virgin · Valiant LadyRound-trip
Caribbean 8 nights Nov 20, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Private Full-Day Curaçao Island Tour with Local Ex…Aruba +2 more
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from $792
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Azamara · Azamara JourneyRound-trip
Caribbean 14 nights Nov 21 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · San Juan, Puerto Rico15 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +9 more
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from $5,762
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Holland America · EurodamRound-trip
Bahamas 14 nights Nov 21 – Dec 5, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · … · Fort Lauderdale (Port Everglades), Florida11 ports
Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Key West, Florida · Fort Lauderdale (Port Everglades), Florida · Grand Turk, Turks and Caicos · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Half Moon Cay (Little San Salvador Island), Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowHorseback Riding by Land & Sea27 Charcos of DamajaguaGibbs Cay Private Stingray Swim & Reef Snorkel +3 more
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from $1,214
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Royal Caribbean · Harmony of the SeasRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Nassau, Bahamas · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Nassau, Bahamas · Perfect Day at CocoCay · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexSwim With the Wild Exuma PigsDaredevil's PeakWalk El Morro & Old San Juan's City Walls +1 more
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from $1,172
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $836
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Explora Journeys · EXPLORA IIIOne-way
Caribbean 7 nights Nov 22, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Saint John/cruz Bay · … · San Juan, Puerto Rico6 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelRandom Wind 'Paradise Day Sail' +1 more
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from $4,200
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Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Nov 22 – Nov 29, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $919
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 14 nights Nov 22 – Dec 6, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Celebration Key, Bahamas · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · Celebration Key, Bahamas · Grand Turk, Turks and Caicos · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowKayak the Lucayan Caves & Gold Rock Beach with the…Gibbs Cay Private Stingray Swim & Reef SnorkelSwim With the Wild Exuma Pigs +3 more
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from $999
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Princess · Sun PrincessRound-trip
Caribbean 7 nights Nov 22 – Nov 29, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Relaxaway, Half Moon Cay · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowWalk El Morro & Old San Juan's City Walls27 Charcos of Damajagua
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from $729
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 22 – Nov 29, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $856
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Nov 22 – Dec 6, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Virgin Gorda, British Virgin Islands · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Island HoppingMt. Liamuiga Volcano Crater Hike +6 more
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from $5,599
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Oceania · Oceania InsigniaRound-trip
Bahamas 25 nights Nov 24 – Dec 19, 2026 from Miami, Florida
Miami, Florida · Tortola, B.V.I. · … · Miami, Florida18 ports
Miami, Florida · Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · Scarborough, Tobago · Kiel Canal, Germany · Santarem, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Alter do Chao, Brazil · Kiel Canal, Germany · Bridgetown, Barbados · Roseau, Dominica · Philipsburg, St. Maarten · San Juan, Puerto Rico · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Jost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +11 more
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from $16,949
Book This Cruise@ Cruisebound
Oceania · Oceania MarinaRepositioning
Mediterranean 15 nights Nov 25 – Dec 10, 2026 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Valencia, Spain · … · Miami, Florida8 ports
Barcelona, Spain · Valencia, Spain · Alicante, Spain · Malaga, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Sagrada FamiliaOceanograficCastillo de Santa BárbaraGranada & the Alhambra +4 more
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from $2,567
Book This Cruise@ Cruisebound
Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 25 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $4,999
Book This Cruise@ Cruisebound
Azamara · Azamara QuestOne-way
Caribbean 21 nights Nov 26 – Dec 17, 2026 from Piraeus (Athens), Greece to Miami, Florida
Piraeus (Athens), Greece · Katakolon (Olympia), Greece · … · Miami, Florida11 ports
Piraeus (Athens), Greece · Katakolon (Olympia), Greece · Syracuse, Sicily · Valletta, Malta · Trapani, Italy · La Goulette, Tunisia · Cartagena, Spain · Malaga, Spain · Tangier, Morocco · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineAncient OlympiaNeapolis Archaeological ParkSt John's Co-Cathedral & the Caravaggio masterpieces +7 more
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from $6,912
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Cunard · Queen ElizabethRound-trip
Caribbean 21 nights Nov 26 – Dec 17, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida14 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsAdventure AntiguaGros Piton Summit Hike +8 more
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from $1,665
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyRound-trip
Caribbean 14 nights Nov 28 – Dec 12, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados15 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +9 more
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from $5,719
Book This Cruise@ Cruisebound
Carnival · Carnival MagicRound-trip
Bahamas 8 nights Nov 28, 2026 from Miami, Florida
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · … · Miami, Florida6 ports
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Horseback Riding by Land & SeaWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail' +1 more
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from $537
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $774
Book This Cruise@ Cruisebound
Holland America · EurodamRound-trip
Bahamas 14 nights Nov 28 – Dec 12, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Grand Turk, Turks and Caicos · … · Fort Lauderdale (Port Everglades), Florida11 ports
Fort Lauderdale (Port Everglades), Florida · Grand Turk, Turks and Caicos · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Half Moon Cay (Little San Salvador Island), Bahamas · Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowGibbs Cay Private Stingray Swim & Reef SnorkelWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter +4 more
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from $1,224
Book This Cruise@ Cruisebound
Holland America · ZuiderdamRound-trip
Caribbean 14 nights Nov 28 – Dec 12, 2026 from Miami, Florida
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · … · Miami, Florida11 ports
Miami, Florida · Half Moon Cay (Little San Salvador Island), Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Nassau, Bahamas · Miami, Florida · Grand Turk, Turks and Caicos · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Half Moon Cay (Little San Salvador Island), Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Horseback Riding by Land & Sea27 Charcos of DamajaguaGibbs Cay Private Stingray Swim & Reef Snorkel +3 more
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from $1,094
Book This Cruise@ Cruisebound
MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Nov 28 – Dec 12, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,246
Book This Cruise@ Cruisebound
Norwegian · Norwegian GemRound-trip
Caribbean 12 nights Nov 28 – Dec 10, 2026 from Tampa, Florida
Tampa, Florida · San Juan, Puerto Rico · … · Tampa, Florida9 ports
Tampa, Florida · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterWalk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +4 more
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from $909
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Nov 28 – Dec 8, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Jost Van DykePrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls
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from $749
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
Caribbean 8 nights Nov 28 – Dec 6, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachWalk El Morro & Old San Juan's City Walls27 Charcos of Damajagua +1 more
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from $773
Book This Cruise@ Cruisebound
Royal Caribbean · Harmony of the SeasRound-trip
Bahamas 7 nights Nov 28, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Philipsburg, St. Maarten · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City WallsDaredevil's Peak
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from $772
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $531
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Virgin · Valiant LadyRound-trip
Caribbean 7 nights Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Norman IslandMt. Liamuiga Volcano Crater Hike +2 more
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from $693
Book This Cruise@ Cruisebound
Carnival · Carnival VeneziaRound-trip
Caribbean 14 nights Nov 29, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · St. Thomas, U.S. Virgin Islands · Antigua, Antigua & Barbuda · Dominica, Caribbean · Bridgetown, Barbados · Grenada, Caribbean · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Adventure AntiguaBoiling Lake & Valley of Desolation +5 more
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from $671
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIIOne-way
Caribbean 14 nights Nov 29, 2026 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · Miami, Florida6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandMt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +2 more
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from $5,585
Book This Cruise@ Cruisebound
Holland America · Nieuw AmsterdamRound-trip
Bahamas 21 nights Nov 29 – Dec 20, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · … · Fort Lauderdale (Port Everglades), Florida15 ports
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · Fort-de-France, Martinique · Bridgetown, Barbados · Scarborough, Tobago · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Key West, Florida · Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · St. John's, Antigua · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Half Moon Cay (Little San Salvador Island), Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowRandom Wind 'Paradise Day Sail'Mount Pelée & Saint-PierreSwim with wild green sea turtles + two shipwrecks… +8 more
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from $2,059
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Bahamas 14 nights Nov 29 – Dec 13, 2026 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida10 ports
Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · San Juan, Puerto Rico · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +4 more
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from $1,106
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 29 – Dec 11, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $879
Book This Cruise@ Cruisebound
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $899
Book This Cruise@ Cruisebound
Princess · Sky PrincessRound-trip
Caribbean 8 nights Nov 29 – Dec 7, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Princess Cays, Bahamas · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Princess Cays, Bahamas · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexPrivate Bungalow DayWalk El Morro & Old San Juan's City Walls27 Charcos of Damajagua +1 more
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from $611
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurRound-trip
Bahamas 10 nights Nov 29 – Dec 9, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandWalk El Morro & Old San Juan's City WallsPrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $6,949
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $542
Book This Cruise@ Cruisebound
Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +3 more
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from $3,913
Book This Cruise@ Cruisebound
Silversea · Silver ShadowRound-trip
Caribbean 10 nights Nov 30 – Dec 10, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Jost Van Dyke, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +2 more
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from $6,450
Book This Cruise@ Cruisebound
Virgin · Brilliant LadyRound-trip
Caribbean 10 nights Nov 30, 2026 from Miami, Florida
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida8 ports
Miami, Florida · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Maho BeachNorman IslandBuck Island Reef +3 more
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from $1,190
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Azamara · Azamara QuestOne-way
Caribbean 13 nights Dec 4 – Dec 17, 2026 from Malaga, Spain to Miami, Florida
Malaga, Spain · Tangier, Morocco · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Granada & the AlhambraTangier Kasbah, Medina & American Legation Private…Walk El Morro & Old San Juan's City WallsStar Island & Millionaire's Row Skyline Cruise on…
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from $2,669
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 7 nights Dec 5 – Dec 12, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +3 more
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from $2,612
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $770
Book This Cruise@ Cruisebound
Holland America · ZuiderdamRound-trip
Bahamas 7 nights Dec 5 – Dec 12, 2026 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida6 ports
Miami, Florida · Grand Turk, Turks and Caicos · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Half Moon Cay (Little San Salvador Island), Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter +1 more
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from $699
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Caribbean 8 nights Dec 5 – Dec 13, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida6 ports
Miami, Florida · San Juan, Puerto Rico · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Island TourPrivate Full-Day Boat Charter +1 more
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from $498
Book This Cruise@ Cruisebound
MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Dec 5 – Dec 19, 2026 from Miami, Florida
Miami, Florida · Roatan, Honduras · … · Miami, Florida10 ports
Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Chacchoben Mayan RuinsEl Cielo + Palancar + Columbia 3-Stop Snorkel +3 more
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from $1,246
Book This Cruise@ Cruisebound
Royal Caribbean · Harmony of the SeasRound-trip
Bahamas 7 nights Dec 5 – Dec 12, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Philipsburg, St. Maarten · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City WallsDaredevil's Peak
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from $936
Book This Cruise@ Cruisebound
Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $519
Book This Cruise@ Cruisebound
Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Dec 5 – Dec 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $5,599
Book This Cruise@ Cruisebound
Virgin · Resilient LadyRound-trip
Caribbean 8 nights Dec 5, 2026 from Miami, Florida
Miami, Florida · St. Croix, U.S. Virgin Islands · … · Miami, Florida6 ports
Miami, Florida · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Buck Island ReefWalk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $792
Book This Cruise@ Cruisebound
Virgin · Valiant LadyRound-trip
Caribbean 7 nights Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $903
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIIOne-way
Caribbean 14 nights Dec 6, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Saint John/cruz Bay · … · San Juan, Puerto Rico6 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Gustavia, St. Barts · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelPrivate Open-Top Mini Moke Island Tour of St. Barts +1 more
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from $4,200
Book This Cruise@ Cruisebound
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Gros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $909
Book This Cruise@ Cruisebound
Princess · Sun PrincessRound-trip
Mexico 14 nights Dec 6 – Dec 20, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Celebration Key, Bahamas · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Celebration Key, Bahamas · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Fort Lauderdale (Port Everglades), Florida · Celebration Key, Bahamas · Cozumel, Mexico · Roatan, Honduras · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowKayak the Lucayan Caves & Gold Rock Beach with the…Walk El Morro & Old San Juan's City Walls27 Charcos of Damajagua +2 more
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from $5,593
Book This Cruise@ Cruisebound
Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $611
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Dec 6 – Dec 20, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Road Bay, Anguilla · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsThe Baths National ParkMt. Liamuiga Volcano Crater Hike +6 more
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from $7,054
Book This Cruise@ Cruisebound
Windstar · Star PrideRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Deshaies, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $3,636
Book This Cruise@ Cruisebound
Royal Caribbean · Jewel of the SeasRound-trip
Caribbean 9 nights Dec 7 – Dec 16, 2026 from Tampa, Florida
Tampa, Florida · San Juan, Puerto Rico · … · Tampa, Florida6 ports
Tampa, Florida · San Juan, Puerto Rico · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Full-Day Boat Charter +1 more
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from $904
Book This Cruise@ Cruisebound
Cunard · Queen ElizabethRound-trip
Caribbean 21 nights Dec 8 – Dec 29, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida13 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarMartha Brae River Bamboo RaftingHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +7 more
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from $1,912
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Dec 8 – Dec 18, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke
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from $689
Book This Cruise@ Cruisebound
Silversea · Silver ShadowOne-way
Caribbean 10 nights Dec 10 – Dec 20, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico9 ports
Miami, Florida · Cruz Bay, St. John, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Iles des Saintes, Guadeloupe · Fort-de-France, Martinique · Little Bay, Montserrat, Leeward Islands · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Trunk Bay Underwater Snorkel Trail & VI National P…Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +5 more
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from $3,850
Book This Cruise@ Cruisebound
Holland America · Nieuw AmsterdamRound-trip
Bahamas 16 nights Dec 11 – Dec 27, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · … · Fort Lauderdale (Port Everglades), Florida12 ports
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · St. John's, Antigua · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Half Moon Cay (Little San Salvador Island), Bahamas · Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · Key West, Florida · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay BeachNorman Island +5 more
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from $1,434
Book This Cruise@ Cruisebound
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 11 – Dec 23, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
★ Bucket-list Manhattan Helicopter TourThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater Hike +3 more
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from $969
Book This Cruise@ Cruisebound
Regent · Seven Seas SplendorRound-trip
Caribbean 17 nights Dec 11 – Dec 28, 2026 from Galveston, Texas
Galveston, Texas · Willis Island · … · Galveston, Texas15 ports
Galveston, Texas · Willis Island · Montego Bay, Jamaica · Ocho Rios, Jamaica · Willis Island · Punta Cana, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Gustavia, St. Barts · St. John's, Antigua · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Galveston, Texas
★ Bucket-list Moody GardensZodiac Circumnavigation of Willis IslandMartha Brae River Bamboo RaftingBlue Hole +7 more
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from $12,699
Book This Cruise@ Cruisebound
Silversea · Silver RayRound-trip
Caribbean 11 nights Dec 11 – Dec 22, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Deshaies, Guadeloupe · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +3 more
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from $5,450
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 6 nights Dec 12 – Dec 18, 2026 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico7 ports
Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursBoiling Lake HikeMt. Liamuiga Volcano Crater Hike +3 more
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from $2,024
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $713
Book This Cruise@ Cruisebound
Disney · Disney DestinyRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Disney Lookout Cay · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City WallsMaho Beach
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from $1,984
Book This Cruise@ Cruisebound
MSC Cruises · MSC World AmericaRound-trip
Bahamas 14 nights Dec 12 – Dec 26, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,456
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $666
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Virgin · Valiant LadyRound-trip
Caribbean 7 nights Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $973
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Carnival · Carnival CelebrationRound-trip
Caribbean 7 nights Dec 13, 2026 from Miami, Florida
Miami, Florida · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Celebration Key, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City WallsKayak the Lucayan Caves & Gold Rock Beach with the…
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from $755
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Carnival · Carnival VeneziaRound-trip
Caribbean 7 nights Dec 13, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Celebration Key, Bahamas · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexKayak the Lucayan Caves & Gold Rock Beach with the…Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…
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from $645
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Celebrity · Celebrity BeyondRound-trip
Bahamas 7 nights Dec 13 – Dec 20, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Puerto Plata, Dominican Republic · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowThe full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterWalk El Morro & Old San Juan's City Walls +1 more
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from $1,080
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Explora Journeys · EXPLORA IOne-way
Caribbean 7 nights Dec 13, 2026 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Saint John/cruz Bay · … · San Juan, Puerto Rico6 ports
Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Half-Day Island Adventure & Trunk Bay BeachPrivate Catamaran Sail & SnorkelRandom Wind 'Paradise Day Sail' +1 more
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from $3,635
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 15 nights Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Grand Turk, Turks and Caicos · Miami, Florida · Ocho Rios, Jamaica · Ain Sokhna, Egypt · Jost Van Dyke, British Virgin Islands · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Island HoppingPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +7 more
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from $12,600
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Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Dec 13 – Dec 20, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $899
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Princess · Sky PrincessRound-trip
Caribbean 8 nights Dec 13 – Dec 21, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Celebration Key, Bahamas · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Celebration Key, Bahamas · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexKayak the Lucayan Caves & Gold Rock Beach with the…Gibbs Cay Private Stingray Swim & Reef Snorkel27 Charcos of Damajagua +1 more
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from $714
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Princess · Sun PrincessRound-trip
Caribbean 14 nights Dec 13 – Dec 27, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Celebration Key, Bahamas · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Celebration Key, Bahamas · Cozumel, Mexico · Roatan, Honduras · Fort Lauderdale (Port Everglades), Florida · San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Celebration Key, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowKayak the Lucayan Caves & Gold Rock Beach with the…El Cielo + Palancar + Columbia 3-Stop SnorkelHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +2 more
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from $6,633
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Regent · Seven Seas PrestigeOne-way
Mediterranean 14 nights Dec 13 – Dec 27, 2026 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Malaga, Spain · Funchal, Madeira, Portugal · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Sagrada FamiliaGranada & the AlhambraPico do Arieiro to Pico RuivoWalk El Morro & Old San Juan's City Walls +1 more
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from $14,899
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Royal Caribbean · Independence of the SeasRound-trip
Bahamas 7 nights Dec 13 – Dec 20, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Daredevil's PeakWalk El Morro & Old San Juan's City WallsPrivate Full-Day Boat Charter
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from $810
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