Bucket-List Cruise Adventures

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Showing 36 of 288 sailings
Princess · Coral PrincessRound-trip
Caribbean 14 nights Oct 15 – Oct 29, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Dominica, Caribbean · St. Georges, Grenada, West Indies · Port of Spain, Trinidad · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +4 more
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from $1,489
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Oceania · Oceania VistaRepositioning
Caribbean 14 nights Oct 28 – Nov 11, 2026 from New York, New York to Miami, Florida
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida10 ports
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Full-Day Boat CharterJost Van DykePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $3,930
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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
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 $1,999
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana
★ Bucket-list Private Luxury Boston TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Gros Piton Summit HikeGrenada Private Taxi Tour +4 more
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from $1,249
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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
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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
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Oceania · Oceania VistaRound-trip
Caribbean 14 nights Nov 11 – Nov 25, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida10 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Falmouth, Jamaica · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue Hole & Secret FallsAruba +5 more
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from $5,025
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Celebrity · Celebrity AscentRound-trip
Caribbean 10 nights Nov 13 – Nov 23, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · … · Fort Lauderdale (Port Everglades), Florida7 ports
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · St. John's, Antigua · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowRandom Wind 'Paradise Day Sail'Cosol ToursGrenada Private Taxi Tour +2 more
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from $1,767
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MSC Cruises · MSC World EuropaRepositioning
Caribbean 21 nights Nov 14 – Dec 5, 2026 from Genoa, Italy to Fort-de-France, Martinique
Genoa, Italy · Civitavecchia (Rome), Italy · … · Fort-de-France, Martinique13 ports
Genoa, Italy · Civitavecchia (Rome), Italy · La Spezia (Cinque Terre), Italy · Marseille, France · Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique
★ Bucket-list Sail straight to Portofino from the cruise dockVatican, Sistine Chapel & Colosseum in One DayPrivate Cinque Terre by Minivan & Ferryboat from L…Calanques National Park Boat Cruise from the Old P… +9 more
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from $1,261
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MSC Cruises · MSC World EuropaRepositioning
Mediterranean 20 nights Nov 15 – Dec 5, 2026 from Civitavecchia (Rome), Italy to Fort-de-France, Martinique
Civitavecchia (Rome), Italy · La Spezia (Cinque Terre), Italy · … · Fort-de-France, Martinique12 ports
Civitavecchia (Rome), Italy · La Spezia (Cinque Terre), Italy · Marseille, France · Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayPrivate Cinque Terre by Minivan & Ferryboat from L…Calanques National Park Boat Cruise from the Old P…Sagrada Familia +8 more
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from $1,130
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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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MSC Cruises · MSC World EuropaRepositioning
Caribbean 19 nights Nov 17 – Dec 6, 2026 from Marseille, France to Pointe-a-Pitre, Guadeloupe
Marseille, France · Barcelona, Spain · … · Pointe-a-Pitre, Guadeloupe11 ports
Marseille, France · Barcelona, Spain · Puerto del Rosario, Spain · Santa Cruz de Tenerife, Canary Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Calanques National Park Boat Cruise from the Old P…Sagrada FamiliaFuerteventuraTeide National Park +7 more
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from $1,274
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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 $5,769
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Windstar · Wind StarOne-way
Caribbean 11 nights Nov 24 – Dec 5, 2026 from Bridgetown, Barbados to Colon, Panama
Bridgetown, Barbados · Bequia, Grenadines · … · Colon, Panama9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Kralendijk, Bonaire · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cartagena, Colombia · San Blas Islands, Panama · Colon, Panama
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourKlein Bonaire +5 more
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from $7,896
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Windstar · Star LegendRound-trip
Mediterranean 7 nights Nov 27 – Dec 4, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Anses D'arlet, Martinique · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Anses D'arlet, Martinique · Rodney Bay, St. Lucia · Casablanca, Morocco · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Small-Boat Snorkel with Wild Sea Turtles, Anse NoireFull-Day Private Catamaran Sail to Soufrière & the…Private Guided Tour of Casablanca with Hassan II M… +3 more
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from $2,594
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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
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Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Nov 28 – Dec 12, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Bridgetown, Barbados13 ports
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 · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Full-Day Private Catamaran Sail to Soufrière & the…Soufrière Hills Volcano Exclusion Zone Helicopter…Private Half-Day Island Adventure & Trunk Bay Beach +7 more
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from $6,479
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 13 nights Dec 2 – Dec 15, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados12 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourMount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga… +5 more
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from $5,271
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Celebrity · Celebrity AscentRound-trip
Caribbean 10 nights Dec 4 – Dec 14, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · … · Fort Lauderdale (Port Everglades), Florida7 ports
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · St. John's, Antigua · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowRandom Wind 'Paradise Day Sail'Cosol ToursGrenada Private Taxi Tour +2 more
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from $2,213
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Windstar · Star LegendOne-way
Caribbean 8 nights Dec 4 – Dec 12, 2026 from Bridgetown, Barbados to Port of Oranjestad, Aruba, Caribbean
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Port of Oranjestad, Aruba, Caribbean8 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Sca · Bequia, Grenadines · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Full-Day Private Catamaran Sail to Soufrière & the…Tobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +3 more
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from $2,940
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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 $2,459
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Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Dec 5 – Dec 19, 2026 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados13 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +7 more
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from $6,319
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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
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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 $728
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from Fort-de-France, Martinique
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · … · Fort-de-France, Martinique7 ports
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Castries, St. Lucia · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Cosol ToursSwim with wild green sea turtles + two shipwrecks… +2 more
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from $694
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 7 nights Dec 13 – Dec 20, 2026 from Pointe-a-Pitre, Guadeloupe
Pointe-a-Pitre, Guadeloupe · Castries, St. Lucia · … · Pointe-a-Pitre, Guadeloupe7 ports
Pointe-a-Pitre, Guadeloupe · Castries, St. Lucia · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Cosol ToursSwim with wild green sea turtles + two shipwrecks…La Soufrière Volcano Summit Hike +2 more
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from $1,029
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Celebrity · Celebrity AscentRound-trip
Caribbean 10 nights Dec 14 – Dec 24, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · … · Fort Lauderdale (Port Everglades), Florida7 ports
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · St. John's, Antigua · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowRandom Wind 'Paradise Day Sail'Cosol ToursGrenada Private Taxi Tour +2 more
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from $1,297
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 14 nights Dec 15 – Dec 29, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · … · Bridgetown, Barbados12 ports
Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · St. John's, Antigua · Port of Charlestown, Nevis, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…La Soufrière Volcano Summit HikeGrenada Private Taxi TourMount Pelée & Saint-Pierre +5 more
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from $1,958
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Silversea · Silver NovaOne-way
Caribbean 8 nights Dec 21 – Dec 29, 2026 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Soufriere, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Soufriere, St. Lucia · Bequia, Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourMount Pelée & Saint-Pierre +3 more
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from $4,050
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Holland America · VolendamRound-trip
Bahamas 14 nights Dec 22 – Jan 5, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Key West, Florida · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · Key West, Florida · Port of Oranjestad, Aruba, Caribbean · Charlotteville, Trinidad and Tobago · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Castries, St. Lucia · 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 ShowDry Tortugas National ParkArubaGrenada Private Taxi Tour +4 more
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from $1,799
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 7 nights Dec 26 – Jan 2, 2027 from Fort-de-France, Martinique
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · … · Fort-de-France, Martinique7 ports
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Castries, St. Lucia · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Swim with wild green sea turtles + two shipwrecks…La Soufrière Volcano Summit Hike +2 more
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from $1,420
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Dec 26 – Jan 2, 2027 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados7 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'The Baths of Virgin GordaMt. Liamuiga Volcano Crater HikeLa Savane des Esclaves +3 more
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from $4,639
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MSC Cruises · MSC World EuropaRound-trip
Caribbean 7 nights Dec 27 – Jan 3, 2027 from Pointe-a-Pitre, Guadeloupe
Pointe-a-Pitre, Guadeloupe · Bridgetown, Barbados · … · Pointe-a-Pitre, Guadeloupe7 ports
Pointe-a-Pitre, Guadeloupe · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. Georges, Grenada, West Indies · Castries, St. Lucia · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Swim with wild green sea turtles + two shipwrecks…La Soufrière Volcano Summit HikeGrenada Private Taxi Tour +2 more
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from $1,753
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Princess · Crown PrincessRound-trip
Caribbean 14 nights Dec 27 – Jan 10, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico13 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Maho BeachAdventure Antigua +5 more
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from $3,046
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Silversea · Silver SpiritRound-trip
Caribbean 8 nights Dec 27 – Jan 4, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Deshaies, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Georges, Grenada, West Indies · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierreJardin Botanique de Deshaies at Opening Hour +3 more
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