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 Antigua ×13+ nights × Clear all
Showing 5 of 5 sailings
Oceania · Oceania VistaRepositioning
Caribbean 14 nights Oct 28 – Nov 11, 2026 from New York, New York to Miami, Florida
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida10 ports
New York, New York · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Full-Day Boat CharterJost Van DykePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $3,412
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Regent · Seven Seas MarinerOne-way
Caribbean 14 nights Apr 15 – Apr 29, 2027 from Miami, Florida to New York, New York
Miami, Florida · Willis Island · … · New York, New York12 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · St. John's, Antigua · Tortola, B.V.I. · Willis Island · New York, New York
★ 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… +5 more
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from $8,199
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Azamara · Azamara QuestOne-way
Caribbean 17 nights Oct 28 – Nov 14, 2027 from New York, New York to Bridgetown, Barbados
New York, New York · Hamilton, Bermuda · … · Bridgetown, Barbados13 ports
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Manhattan Helicopter TourRandom Wind 'Paradise Day Sail'Norman IslandWalk El Morro & Old San Juan's City Walls +6 more
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from $5,583
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Oceania · Oceania SirenaRepositioning
Caribbean 15 nights Nov 6 – Nov 21, 2027 from New York, New York to Miami, Florida
New York, New York · Tortola, B.V.I. · … · Miami, Florida10 ports
New York, New York · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida
★ Bucket-list Manhattan Helicopter TourJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +6 more
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from $4,199
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Princess · Regal PrincessRepositioning
Caribbean 14 nights Nov 6 – Nov 20, 2027 from New York, New York to Miami, Florida
New York, New York · St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
New York, New York · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeAdventure Antigua +5 more
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from $1,324
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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