Bucket-List Cruise Adventures

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Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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Showing 36 of 730 sailings
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 $598
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Norwegian · Norwegian LunaRound-trip
Bahamas 7 nights Sep 19 – Sep 26, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $329
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Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Sep 20 – Sep 27, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $729
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Norwegian · Norwegian LunaRound-trip
Bahamas 7 nights Sep 26 – Oct 3, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $459
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Celebrity · Celebrity BeyondRound-trip
Caribbean 7 nights Sep 27, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Tortola, B.V.I. · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsJost Van DykeRandom Wind 'Paradise Day Sail'
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from $1,149
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Virgin · Resilient LadyRound-trip
Bahamas 5 nights Sep 28, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsSwim with Wild Dolphins at Honeymoon Harbour
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from $845
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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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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 $513
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Norwegian · Norwegian LunaRound-trip
Bahamas 7 nights Oct 3 – Oct 10, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $559
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Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Oct 4 – Oct 11, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $759
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MSC Cruises · MSC World AmericaRound-trip
Bahamas 14 nights Oct 10 – Oct 24, 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 $1,619
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Norwegian · Norwegian LunaRound-trip
Bahamas 7 nights Oct 10 – Oct 17, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $689
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Royal Caribbean · Adventure of the SeasRound-trip
Bahamas 6 nights Oct 10 – Oct 16, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Nassau, Bahamas · Puerto Plata, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexSwim With the Wild Exuma PigsThe full 27 jumps at the Damajagua WaterfallsGibbs Cay Private Stingray Swim & Reef Snorkel
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from $703
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Celebrity · Celebrity BeyondRound-trip
Caribbean 7 nights Oct 11, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsJost Van DykeMt. Liamuiga Volcano Crater Hike
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from $1,234
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Virgin · Resilient LadyRound-trip
Caribbean 5 nights Oct 12, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsSwim with Wild Dolphins at Honeymoon Harbour
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from $545
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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 $1,413
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Norwegian · Norwegian LunaRound-trip
Caribbean 7 nights Oct 17 – Oct 24, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $589
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Norwegian · Norwegian PrimaRound-trip
Bahamas 7 nights Oct 18 – Oct 25, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $559
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Norwegian · Norwegian LunaRound-trip
Caribbean 7 nights Oct 24 – Oct 31, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $529
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Celebrity · Celebrity BeyondRound-trip
Caribbean 7 nights Oct 25, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Tortola, B.V.I. · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsJost Van DykeRandom Wind 'Paradise Day Sail'
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from $1,524
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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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Virgin · Scarlet LadyRound-trip
Bahamas 6 nights Oct 25, 2026 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelThe full 27 jumps at the Damajagua WaterfallsSwim with Wild Dolphins at Honeymoon Harbour
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from $1,134
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Norwegian · Norwegian GetawayRound-trip
Bahamas 5 nights Oct 28 – Nov 2, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsSilver Cove Private Villa
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from $379
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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 IslandBahía de las ÁguilasArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +2 more
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from $1,848
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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 $1,210
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Norwegian · Norwegian LunaRound-trip
Caribbean 7 nights Oct 31 – Nov 7, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida6 ports
Miami, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $539
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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 $2,050
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Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Nov 1 – Nov 8, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · Puerto Plata, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke +1 more
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from $579
Book This Cruise@ Cruisebound
Oceania · Oceania InsigniaOne-way
Mediterranean 47 nights Nov 2 – Dec 19, 2026 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Palma de Mallorca, Spain · … · Miami, Florida29 ports
Barcelona, Spain · Palma de Mallorca, Spain · Alicante, Spain · Cartagena, Spain · Malaga, Spain · Seville, Spain · Portimao, Portugal · Lisbon, Portugal · Arrecife, Lanzarote, Canary Islands · Las Palmas, Gran Canaria, Canary Islands · Santa Cruz de La Palma, Spain · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida · Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · Scarborough, Tobago · Santarem, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Alter do Chao, Brazil · Bridgetown, Barbados · Roseau, Dominica · Philipsburg, St. Maarten · San Juan, Puerto Rico · Nassau, Bahamas · Miami, Florida
★ Bucket-list Sagrada FamiliaLa Seu Cathedral + Rooftop Terraces ClimbCastillo de Santa BárbaraThe Roman Theatre of Cartagena with the Rafael Mon… +22 more
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from $17,099
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Norwegian · Norwegian GetawayRound-trip
Bahamas 5 nights Nov 6 – Nov 11, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsSilver Cove Private Villa
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from $329
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2026 from Port Canaveral, 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 $2,023
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MSC Cruises · MSC World AmericaRound-trip
Bahamas 14 nights Nov 7 – Nov 21, 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 $1,220
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Celebrity · Celebrity XcelRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Full-Day Boat CharterThe full 27 jumps at the Damajagua Waterfalls
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from $1,735
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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
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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 Norwegian AmaWaterways Costa Princess Celebrity Avalon Disney Viking Ocean Holland America Silversea Oceania Virgin Regent Explora Journeys Cunard Azamara Windstar Seabourn Virgin Voyages