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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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 Bahamas ×Seabourn ×9–12 nights × Clear all
Showing 5 of 5 sailings
Seabourn · Seabourn QuestRepositioning
Mediterranean 12 nights Nov 10 – Nov 22, 2026 from Lisbon, Portugal to Miami, Florida
Lisbon, Portugal · Funchal, Madeira, Portugal · Miami, Florida
★ Bucket-list SintraPico do Arieiro to Pico RuivoStar Island & Millionaire's Row Skyline Cruise on…
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from $4,831
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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
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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 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 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
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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.

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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