Bucket-List Cruise Adventures

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Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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Filtering Regent ×Visits Port of Basseterre × Clear all
Showing 18 of 18 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 GrandeurRound-trip
Caribbean 10 nights Dec 19 – Dec 29, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida9 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterBoiling Lake Hike +3 more
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from $8,999
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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 PrestigeRound-trip
Caribbean 12 nights Mar 5 – Mar 17, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida11 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike +5 more
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from $11,099
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Regent · Seven Seas PrestigeOne-way
Bahamas 10 nights Mar 30 – Apr 9, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida11 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +6 more
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from $6,049
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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 PrestigeRound-trip
Caribbean 11 nights Dec 7 – Dec 18, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterPrivate Half-Day Island Adventure & Trunk Bay Beach +4 more
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from $7,649
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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… +4 more
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from $7,799
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Regent · Seven Seas PrestigeRound-trip
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · St. John's, Antigua · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls +4 more
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from $7,099
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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 PrestigeRound-trip
Caribbean 10 nights Jan 7 – Jan 17, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida9 ports
Miami, Florida · Willis Island · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandRandom Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +2 more
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from $7,299
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Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Jan 15 – Jan 25, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Willis Island · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourCosol ToursMount Pelée & Saint-Pierre +4 more
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from $7,199
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Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Jan 25 – Feb 4, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · … · Bridgetown, Barbados10 ports
Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursMount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga… +3 more
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from $6,199
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Regent · Seven Seas PrestigeRound-trip
Caribbean 9 nights Jan 27 – Feb 5, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida8 ports
Miami, Florida · Willis Island · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Philipsburg, St. Maarten · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandMt. Liamuiga Volcano Crater HikeCosol Tours +1 more
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from $7,099
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Feb 4 – Feb 14, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourZodiac Circumnavigation of Willis IslandThe Natural Pool +5 more
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from $5,899
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Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Feb 14 – Feb 24, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Willis Island · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourCosol ToursMount Pelée & Saint-Pierre +4 more
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from $6,099
Book This Cruise@ Cruisebound
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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Regent · Seven Seas GrandeurRound-trip
Caribbean 12 nights Mar 20 – Apr 1, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida12 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · Cayo Levantado, Dominican Republic · San Juan, Puerto Rico · Gustavia, St. Barts · Roseau, Dominica · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls +4 more
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from $7,599
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