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
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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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 4 of 4 sailings
Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Nov 22 – Dec 6, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Virgin Gorda, British Virgin Islands · 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 HikeBoiling Lake Hike +3 more
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from $7,753
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Seabourn · Seabourn QuestRound-trip
Caribbean 14 nights Dec 6 – Dec 20, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida11 ports
Miami, Florida · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Fort-de-France, Martinique · Terre-de-haut, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Road Bay, Anguilla · 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 WallsThe Baths National ParkMt. Liamuiga Volcano Crater Hike +3 more
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from $5,498
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Azamara · Azamara JourneyOne-way
Caribbean 17 nights Dec 28 – Jan 14, 2027 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida14 ports
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Castries, St. Lucia · Port of Charlestown, Nevis, St. Kitts and Nevis · Frederikstad, St. Croix · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Cosol Tours +9 more
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from $7,329
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Azamara · Azamara OnwardRound-trip
Bahamas 14 nights Dec 22 – Jan 5, 2028 from Miami, Florida
Miami, Florida · Bimini, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Bimini, Bahamas · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint- Pierre · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim with Wild Dolphins at Honeymoon HarbourThe Baths National ParkRandom Wind 'Paradise Day Sail' +4 more
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from $5,574
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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