Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

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

When are you free? — only cruises that fit entirely inside your dates
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Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
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Luxury Azamara Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering Seabourn ×Visits Port of Basseterre ×9–12 nights × Clear all
Showing 6 of 6 sailings
Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Nov 13 – Nov 23, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · 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 WallsMt. Liamuiga Volcano Crater Hike
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from $4,498
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 11 nights Nov 23 – Dec 4, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Gustavia, St. Barts · Little Bay, Montserrat, Leeward Islands · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · 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 WallsBoiling Lake HikeMt. Liamuiga Volcano Crater Hike
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from $5,098
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Philipsburg, St. Maarten10 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port Elizabeth, Saint Vincent · Saint-Pierre, Newfoundland, Canada · Terre-de-haut, Guadeloupe · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Road Bay, Anguilla · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourSchotia Private Game ReservePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $5,998
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Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · 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 WallsMt. Liamuiga Volcano Crater Hike
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from $5,498
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 11 nights Dec 28 – Jan 8, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados10 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Road Bay, Anguilla · Falmouth Harbour, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +2 more
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from $6,498
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Seabourn · Seabourn QuestRound-trip
Caribbean 10 nights Dec 28 – Jan 7, 2028 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Gustavia, St. Barts · 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 WallsMt. Liamuiga Volcano Crater Hike
View →
from $5,498
Book This Cruise@ Cruisebound

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.

19 lines
aboard
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