Bucket-List Cruise Adventures

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Showing 36 of 483 sailings
Royal Caribbean · Oasis of the SeasRound-trip
Caribbean Jun 19, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Nassau, Bahamas · Perfect Day at CocoCay · Puerto Plata, Dominican Republic · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandSwim With the Wild Exuma PigsDaredevil's PeakThe full 27 jumps at the Damajagua Waterfalls
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from $2,248
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Jun 27 – Jul 4, 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 $1,504
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Royal Caribbean · Independence of the SeasRound-trip
Bermuda 9 nights Jul 2 – Jul 11, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Island Wrap-Around Van Tour of BermudaRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $1,677
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Jul 11 – Jul 18, 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 $1,269
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Jul 25 – Aug 1, 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 $1,212
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Royal Caribbean · Independence of the SeasRound-trip
Caribbean 9 nights Jul 30 – Aug 8, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Island Wrap-Around Van Tour of BermudaRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $1,300
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Aug 8 – Aug 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 $755
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Aug 22 – Aug 29, 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 $738
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Sep 5 – Sep 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 $616
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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 $678
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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 $598
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Norwegian · Norwegian VivaRepositioning
Caribbean 17 nights Oct 14 – Oct 31, 2026 from Barcelona, Spain to Galveston, Texas
Barcelona, Spain · Alicante, Spain · … · Galveston, Texas9 ports
Barcelona, Spain · Alicante, Spain · Motril, Spain · Funchal, Madeira, Portugal · Philipsburg, St. Maarten · La Romana, Dominican Republic · Cabo Rojo, Dominican Republic · Falmouth, Jamaica · Galveston, Texas
★ Bucket-list Sagrada FamiliaCastillo de Santa BárbaraPico do Arieiro to Pico RuivoRandom Wind 'Paradise Day Sail' +3 more
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from $1,149
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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 $597
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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 Gibbs Cay Private Stingray Swim & Reef SnorkelRandom Wind 'Paradise Day Sail'Boiling Lake HikeMount Pelée & Saint-Pierre +3 more
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from $916
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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 $979
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MSC Cruises · MSC OperaRepositioning
Mediterranean 18 nights Oct 29 – Nov 16, 2026 from Civitavecchia (Rome), Italy to La Romana, Dominican Republic
Civitavecchia (Rome), Italy · Genoa, Italy · … · La Romana, Dominican Republic10 ports
Civitavecchia (Rome), Italy · Genoa, Italy · Livorno (Florence/Pisa), Italy · Marseille, France · Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DaySail straight to Portofino from the cruise dockClimb the Leaning Tower of PisaCalanques National Park Boat Cruise from the Old P… +6 more
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from $1,016
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Royal Caribbean · Independence of the SeasRepositioning
Caribbean 10 nights Oct 29 – Nov 8, 2026 from Cape Liberty (Bayonne), New Jersey to Miami, Florida
Cape Liberty (Bayonne), New Jersey · Cabo Rojo, Dominican Republic · … · Miami, Florida6 ports
Cape Liberty (Bayonne), New Jersey · Cabo Rojo, Dominican Republic · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Statue of Liberty & Ellis IslandArubaPrivate Full-Day Curaçao Island Tour with Local Ex…The full 27 jumps at the Damajagua Waterfalls +1 more
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from $486
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MSC Cruises · MSC OperaRepositioning
Mediterranean 17 nights Oct 30 – Nov 16, 2026 from Genoa, Italy to La Romana, Dominican Republic
Genoa, Italy · Livorno (Florence/Pisa), Italy · … · La Romana, Dominican Republic9 ports
Genoa, Italy · Livorno (Florence/Pisa), Italy · Marseille, France · Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic
★ Bucket-list Sail straight to Portofino from the cruise dockClimb the Leaning Tower of PisaCalanques National Park Boat Cruise from the Old P…Sagrada Familia +5 more
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from $1,246
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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 $750
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Carnival · Carnival PrideRound-trip
Caribbean Nov 1, 2026 from Baltimore, Maryland
Baltimore, Maryland · St. Thomas, U.S. Virgin Islands · … · Baltimore, Maryland8 ports
Baltimore, Maryland · St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Amber Cove, Dominican Republic · Baltimore, Maryland
★ Bucket-list Private Catamaran Sail & Snorkel at Honeymoon Beac…Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeAruba +2 more
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from $2,587
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MSC Cruises · MSC OperaRepositioning
Mediterranean 19 nights Nov 1 – Nov 20, 2026 from Marseille, France to Fort-de-France, Martinique
Marseille, France · Barcelona, Spain · … · Fort-de-France, Martinique10 ports
Marseille, France · Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique
★ Bucket-list Calanques National Park Boat Cruise from the Old P…Sagrada FamiliaTangier Kasbah, Medina & American Legation Private…Private Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $1,554
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MSC Cruises · MSC OperaRepositioning
Mediterranean 14 nights Nov 2 – Nov 16, 2026 from Barcelona, Spain to La Romana, Dominican Republic
Barcelona, Spain · Tangier, Morocco · … · La Romana, Dominican Republic6 ports
Barcelona, Spain · Tangier, Morocco · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · La Romana, Dominican Republic
★ Bucket-list Sagrada FamiliaTangier Kasbah, Medina & American Legation Private…Private Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $961
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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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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $938
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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 $581
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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 $601
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Carnival · Carnival MiracleRound-trip
Bahamas Nov 9, 2026 from Galveston, Texas
Galveston, Texas · Celebration Key, Bahamas · … · Galveston, Texas6 ports
Galveston, Texas · Celebration Key, Bahamas · Half Moon Cay (Little San Salvador Island), Bahamas · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · Galveston, Texas
★ Bucket-list Moody GardensKayak the Lucayan Caves & Gold Rock Beach with the…Horseback Riding by Land & SeaGibbs Cay Private Stingray Swim & Reef Snorkel +1 more
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from $724
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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 $447
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Azamara · Azamara JourneyRound-trip
Caribbean 14 nights Nov 14 – Nov 28, 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 · Road Town, Tortola, B.V.I. · 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 +8 more
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from $4,856
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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 $576
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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 +12 more
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from $7,799
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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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MSC Cruises · MSC OperaRound-trip
Caribbean 7 nights Nov 16 – Nov 23, 2026 from La Romana, Dominican Republic
La Romana, Dominican Republic · Catalina Island, Dominican Republic · … · La Romana, Dominican Republic7 ports
La Romana, Dominican Republic · Catalina Island, Dominican Republic · Bridgetown, Barbados · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Saona Island Private Speedboat & Natural Pool DayPrivate Wildlands Eco TourSwim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more
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from $1,407
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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 $917
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Seabourn · Seabourn OvationOne-way
Caribbean 8 nights Nov 20 – Nov 28, 2026 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados7 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
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $4,098
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,788
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Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.

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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara