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 1 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
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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+ pick specific cruise lines · 1 selected
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 Caribbean ×Celebrity ×9–12 nights × Clear all
Showing 6 of 6 sailings
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 +4 more
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from $917
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Celebrity · Celebrity SummitRound-trip
Mexico 9 nights Jan 3 – Jan 12, 2027 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Tampa, Florida7 ports
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Chacchoben Mayan Ruins +1 more
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from $699
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Celebrity · Celebrity SummitRound-trip
Mexico 10 nights Feb 14 – Feb 24, 2027 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · … · Tampa, Florida8 ports
Tampa, Florida · Cozumel, Mexico · Belize City, Belize · Costa Maya, Mexico · Roatan, Honduras · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno…Chacchoben Mayan Ruins +3 more
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from $837
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Celebrity · Celebrity SummitRepositioning
Caribbean 9 nights Oct 20 – Oct 29, 2027 from Boston, Massachusetts to San Juan, Puerto Rico
Boston, Massachusetts · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Boston, Massachusetts · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Private Luxury Boston TourThe full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $806
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Celebrity · Celebrity SummitRound-trip
Caribbean 9 nights Oct 29 – Nov 7, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. John's, Antigua · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachCosol ToursGrenada Private Taxi Tour +2 more
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from $879
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Celebrity · Celebrity ApexRound-trip
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Orlando, Florida
Orlando, Florida · Philipsburg, St. Maarten · … · Orlando, Florida7 ports
Orlando, Florida · Philipsburg, St. Maarten · Castries, St. Lucia · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Grand Turk, Turks and Caicos · Orlando, Florida
★ Bucket-list Random Wind 'Paradise Day Sail'Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachPrivate Full-Day Boat Charter +1 more
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from $2,167
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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
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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