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 2 selected · clear Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
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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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Showing 3 of 3 sailings
Regent · Seven Seas MarinerOne-way
Caribbean 10 nights Dec 1 – Dec 11, 2026 from Miami, Florida to Tampa, Florida
Miami, Florida · Willis Island · … · Tampa, Florida10 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Tampa, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +3 more
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from $7,900
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Regent · Seven Seas MarinerOne-way
Caribbean 14 nights Dec 21 – Jan 4, 2027 from Tampa, Florida to Miami, Florida
Tampa, Florida · Willis Island · … · Miami, Florida14 ports
Tampa, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterZodiac Circumnavigation of Willis IslandStingray City SandbarThe Natural Pool +6 more
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from $9,899
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Azamara · Azamara QuestRound-trip
Caribbean 11 nights Mar 22 – Apr 2, 2028 from Miami, Florida
Miami, Florida · Key West, Florida · … · Miami, Florida7 ports
Miami, Florida · Key West, Florida · Tampa, Florida · Mobile, Alabama · New Orleans, Louisiana · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkClearwater Beach Private Luxury CharterSteamboat Natchez +1 more
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from $3,521
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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.

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