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 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 Regent ×Visits Port of Basseterre ×13+ nights × Clear all
Showing 6 of 6 sailings
Regent · Seven Seas SplendorOne-way
Australia & South Pacific 16 nights Oct 30 – Nov 15, 2026 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida14 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Willis Island · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · San Juan, Puerto Rico · Willis Island · Miami, Florida
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & Lunenburg +6 more
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from $11,950
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Regent · Seven Seas MarinerOne-way
Caribbean 14 nights Dec 21 – Jan 4, 2027 from Tampa, Florida to Miami, Florida
Tampa, Florida · Willis Island · … · Miami, Florida14 ports
Tampa, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterZodiac Circumnavigation of Willis IslandStingray City SandbarThe Natural Pool +6 more
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from $9,899
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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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Regent · Seven Seas GrandeurRound-trip
Caribbean 14 nights Dec 8 – Dec 22, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida14 ports
Miami, Florida · Willis Island · Ocho Rios, Jamaica · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Willis Island · Miami, Florida
★ 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 $7,799
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Regent · Seven Seas VoyagerRound-trip
Mediterranean 25 nights Dec 19 – Jan 13, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida26 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Oranjestad, Sint Eustatius · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Willis Island · Cartagena, Spain · Panama Canal, Panama · Colon, Panama · Puerto Limon, Costa Rica · Willis Island · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykePrivate Full-Day Boat Charter +14 more
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from $14,049
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Regent · Seven Seas VoyagerOne-way
Caribbean 21 nights Feb 26 – Mar 18, 2028 from Rio de Janeiro, Brazil to Miami, Florida
Rio de Janeiro, Brazil · Willis Island · … · Miami, Florida14 ports
Rio de Janeiro, Brazil · Willis Island · Recife, Brazil · Willis Island · Alter do Chao, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Santarem, Brazil · Willis Island · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Willis Island · Miami, Florida
★ Bucket-list Private Full-Day Rio HighlightsZodiac Circumnavigation of Willis IslandCosol ToursMt. Liamuiga Volcano Crater Hike +1 more
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from $20,699
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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