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 13 of 13 sailings
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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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 +1 more
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from $4,098
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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'Mt. Liamuiga Volcano Crater HikeGrenada Private Taxi TourSwim with wild green sea turtles + two shipwrecks… +1 more
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from $6,798
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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 +2 more
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from $1,645
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Royal Caribbean · Rhapsody of the SeasOne-way
Caribbean 10 nights Mar 6 – Mar 16, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida9 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Miami, Florida
★ 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 +5 more
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from $729
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Regent · Seven Seas PrestigeOne-way
Caribbean 10 nights Mar 20 – Mar 30, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Willis Island · … · San Juan, Puerto Rico10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterBoiling Lake Hike +6 more
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from $6,099
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Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Apr 4 – Apr 14, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 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 · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +5 more
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from $792
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Azamara · Azamara QuestOne-way
Caribbean 7 nights Nov 28 – Dec 5, 2027 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 · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · 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 $2,449
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Azamara · Azamara QuestOne-way
Caribbean 7 nights Dec 12 – Dec 19, 2027 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 +3 more
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from $2,383
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Regent · Seven Seas GrandeurOne-way
Caribbean 10 nights Jan 5 – Jan 15, 2028 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Willis Island · … · Bridgetown, Barbados10 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Philipsburg, St. Maarten · Pointe-a-Pitre, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykeRandom Wind 'Paradise Day Sail' +5 more
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from $6,399
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Regent · Seven Seas GrandeurOne-way
Caribbean 9 nights Feb 24 – Mar 4, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Castries, St. Lucia · … · Miami, Florida9 ports
Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Roseau, Dominica · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Philipsburg, St. Maarten · Willis Island · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursMount Pelée & Saint-PierreBoiling Lake Hike +4 more
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from $5,899
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Azamara · Azamara QuestOne-way
Caribbean 9 nights Mar 13 – Mar 22, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Miami, Florida8 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Castries, St. Lucia · Saint- Pierre · Roseau, Dominica · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourCosol ToursBoiling Lake Hike +3 more
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from $3,932
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Regent · Seven Seas PrestigeOne-way
Mediterranean 12 nights Mar 14 – Mar 26, 2028 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida12 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Willis Island · St. Georges, Grenada, West Indies · Roseau, Dominica · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Willis Island · Miami, Florida
★ Bucket-list The Roman Theatre of Cartagena with the Rafael Mon…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +4 more
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from $8,599
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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