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 Bermuda ×Visits Bermuda ×9–12 nights × Clear all
Showing 4 of 4 sailings
Norwegian · Norwegian JewelRound-trip
Bermuda 9 nights Aug 27 – Sep 5, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Saint John, New Brunswick · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $774
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Azamara · Azamara JourneyOne-way
Bermuda 9 nights Oct 29 – Nov 7, 2026 from New York, New York to San Juan, Puerto Rico
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourRising Son CatamaranRandom Wind 'Paradise Day Sail'Norman Island +1 more
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from $1,609
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Norwegian · Norwegian PearlRound-trip
Bermuda 11 nights Mar 28 – Apr 8, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaJost Van DykePrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls +1 more
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from $1,279
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Norwegian · Norwegian PrimaOne-way
Caribbean 10 nights Nov 3 – Nov 13, 2027 from New York, New York to San Juan, Puerto Rico
New York, New York · Royal Naval Dockyard, Bermuda · … · San Juan, Puerto Rico9 ports
New York, New York · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. John's, Antigua · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaJost Van DykeMt. Liamuiga Volcano Crater Hike +5 more
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from $1,554
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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