Bucket-List Cruise Adventures

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Showing 32 of 32 sailings
Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 7, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,755
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 14, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandPrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +1 more
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from $1,153
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,335
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 26, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort-de-France, Martinique · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachMount Pelée & Saint-PierreSwim with wild green sea turtles + two shipwrecks… +2 more
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from $2,039
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 2, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,213
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Regent · Seven Seas MarinerOne-way
Caribbean 18 nights Jan 4 – Jan 22, 2027 from Miami, Florida to Rio de Janeiro, Brazil
Miami, Florida · Willis Island · … · Rio de Janeiro, Brazil17 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Willis Island · Devils Island, French Guiana · Willis Island · Belem, Brazil · Willis Island · Recife, Brazil · Maceio, Brazil · Bahia de Salvador, Brazil · Willis Island · Buzios, Brazil · Rio de Janeiro, Brazil
★ 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 +3 more
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from $12,760
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 16, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,271
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 23, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandMt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $1,127
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 20, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandCosol ToursSwim with wild green sea turtles + two shipwrecks… +2 more
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from $1,273
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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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Virgin Voyages · Valiant LadyRound-trip
Caribbean Mar 6, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,283
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Mar 13, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandMt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $1,187
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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 GrandeurOne-way
Mediterranean 14 nights Mar 31 – Apr 14, 2027 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida14 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Santa Marta, Colombia · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list The Roman Theatre of Cartagena with the Rafael Mon…The Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +5 more
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from $8,699
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Regent · Seven Seas PrestigeOne-way
Bermuda 14 nights Apr 9 – Apr 23, 2027 from Miami, Florida to New York, New York
Miami, Florida · Willis Island · … · New York, New York13 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · San Juan, Puerto Rico · Willis Island · Royal Naval Dockyard, Bermuda · 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… +6 more
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from $10,199
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Nov 12, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks… +3 more
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from $1,134
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Nov 27, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $932
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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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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Dec 11, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · St. John's, Antigua · Castries, St. Lucia · Port of Oranjestad, Aruba, Caribbean · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachPrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +1 more
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from $997
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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 +15 more
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from $14,049
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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 TourLa Soufrière Volcano Summit HikeCosol Tours +5 more
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from $7,199
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Jan 22, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaCosol ToursPrivate Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $973
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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…La Soufrière Volcano Summit HikeCosol ToursMount Pelée & Saint-Pierre +4 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
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Feb 12, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
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from $1,057
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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 TourLa Soufrière Volcano Summit HikeCosol Tours +5 more
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from $6,099
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Regent · Seven Seas PrestigeRound-trip
Caribbean 15 nights Feb 16 – Mar 2, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida15 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Oranjestad, Sint Eustatius · Willis Island · 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 DykeBoiling Lake Hike +7 more
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from $11,799
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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 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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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Mar 18, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaCosol ToursPrivate Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $1,113
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Apr 8, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
View →
from $1,118
Book This Cruise@ Cruisebound

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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