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 Caribbean ×Regent ×9–12 nights × Clear all
Showing 14 of 14 sailings
Regent · Seven Seas SplendorRound-trip
Mexico 11 nights Nov 30 – Dec 11, 2026 from Galveston, Texas
Galveston, Texas · Willis Island · … · Galveston, Texas10 ports
Galveston, Texas · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Roatan, Honduras · Belize City, Belize · Costa Maya, Mexico · Cozumel, Mexico · Willis Island · Galveston, Texas
★ Bucket-list Moody GardensZodiac Circumnavigation of Willis IslandStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +3 more
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from $7,799
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Regent · Seven Seas MarinerOne-way
Caribbean 10 nights Dec 1 – Dec 11, 2026 from Miami, Florida to Tampa, Florida
Miami, Florida · Willis Island · … · Tampa, Florida10 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Tampa, 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… +3 more
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from $7,900
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Regent · Seven Seas MarinerRound-trip
Caribbean 10 nights Dec 11 – Dec 21, 2026 from Tampa, Florida
Tampa, Florida · Willis Island · … · Tampa, Florida11 ports
Tampa, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Willis Island · Roatan, Honduras · Belize City, Belize · Costa Maya, Mexico · Cozumel, Mexico · Willis Island · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterZodiac Circumnavigation of Willis IslandStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +3 more
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from $7,499
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Regent · Seven Seas PrestigeOne-way
Mexico 12 nights Feb 10 – Feb 22, 2027 from Los Angeles, California to Panama City, Panama
Los Angeles, California · Willis Island · … · Panama City, Panama12 ports
Los Angeles, California · Willis Island · Cabo San Lucas, Mexico · Mazatlan, Mexico · Willis Island · Acapulco, Mexico · Willis Island · Puerto Quetzal, Guatemala · Willis Island · Puntarenas, Costa Rica · Willis Island · Panama City, Panama
★ Bucket-list Warner Bros. Studio Tour HollywoodZodiac Circumnavigation of Willis IslandEl Arco & Lover's BeachIsla de Venados
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from $7,549
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Regent · Seven Seas PrestigeOne-way
Caribbean 10 nights Mar 20 – Mar 30, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Willis Island · … · San Juan, Puerto Rico10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterBoiling Lake Hike +6 more
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from $6,099
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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 GrandeurOne-way
Caribbean 10 nights Jan 5 – Jan 15, 2028 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Willis Island · … · Bridgetown, Barbados10 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Philipsburg, St. Maarten · Pointe-a-Pitre, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykeRandom Wind 'Paradise Day Sail' +5 more
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from $6,399
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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 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
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Regent · Seven Seas GrandeurOne-way
Caribbean 9 nights Feb 24 – Mar 4, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Castries, St. Lucia · … · Miami, Florida9 ports
Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Roseau, Dominica · Pointe-a-Pitre, Guadeloupe · Gustavia, St. Barts · Philipsburg, St. Maarten · Willis Island · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursMount Pelée & Saint-PierreBoiling Lake Hike +4 more
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from $5,899
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Regent · Seven Seas PrestigeOne-way
Mediterranean 12 nights Mar 2 – Mar 14, 2028 from Miami, Florida to Panama City, Panama
Miami, Florida · Key West, Florida · … · Panama City, Panama13 ports
Miami, Florida · Key West, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Falmouth, Jamaica · Willis Island · Cabo Rojo, Dominican Republic · Willis Island · Cartagena, Spain · Willis Island · Puerto Limon, Costa Rica · Kiel Canal, Germany · Panama City, Panama
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkZodiac Circumnavigation of Willis IslandStingray City Sandbar +2 more
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from $8,799
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Regent · Seven Seas PrestigeOne-way
Mediterranean 12 nights Mar 14 – Mar 26, 2028 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida12 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Willis Island · St. Georges, Grenada, West Indies · Roseau, Dominica · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Willis Island · Miami, Florida
★ Bucket-list The Roman Theatre of Cartagena with the Rafael Mon…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +4 more
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from $8,599
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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.

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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