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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Showing 36 of 41 sailings
Seabourn · Seabourn VentureRepositioning
Caribbean 24 nights Oct 5 – Oct 29, 2026 from Halifax, Nova Scotia to Rio de Janeiro, Brazil
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Rio de Janeiro, Brazil14 ports
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Rodney Bay, St. Lucia · Bridgetown, Barbados · Port of Spain, Trinidad · Devils Island, French Guiana · Crossing The Equator · Fortaleza, Brazil · Natal(Rio Grande do Norte), Brazil · Bahia de Salvador, Brazil · Buzios, Brazil · Paraty, Brazil · Rio de Janeiro, Brazil
★ Bucket-list Peggy's Cove & LunenburgMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks…Private Full-Day Rio Highlights
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from $12,798
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Nov 28 – Dec 5, 2026 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Virgin Gorda, British Virgin Islands · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater HikeThe Baths National Park +1 more
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from $4,098
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Dec 5 – Dec 19, 2026 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados13 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +2 more
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from $6,798
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Seabourn · Seabourn OvationRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Mt. Liamuiga Volcano Crater HikeBoiling Lake Hike
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from $3,798
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Dec 19 – Jan 2, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +3 more
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from $9,598
Book This Cruise@ Cruisebound
Seabourn · Seabourn QuestRound-trip
Caribbean 16 nights Dec 20 – Jan 5, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida13 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Marigot, Saint Martin · Terre-de-haut, Guadeloupe · Fort-de-France, Martinique · Rodney Bay, St. Lucia · Roseau, Dominica · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeMount Pelée & Saint-Pierre +2 more
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from $10,998
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Seabourn · Seabourn OvationRound-trip
Caribbean 7 nights Jan 2 – Jan 9, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Bridgetown, Barbados6 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Full-Day Curaçao Island Tour with Local Ex…ArubaKlein Bonaire
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from $3,998
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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
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Jan 9 – Jan 23, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +3 more
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from $10,598
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Jan 23 – Feb 6, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +3 more
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from $10,298
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 7 nights Feb 6 – Feb 13, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Bridgetown, Barbados7 ports
Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Saint-Pierre, Newfoundland, Canada · Roseau, Dominica · Terre-de-haut, Guadeloupe · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Mt. Liamuiga Volcano Crater HikeBoiling Lake Hike
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from $5,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Feb 13 – Feb 27, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +3 more
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from $11,298
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Feb 27 – Mar 6, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +1 more
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from $4,798
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Mar 13 – Mar 27, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +3 more
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from $9,498
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRepositioning
Mediterranean 22 nights Mar 27 – Apr 18, 2027 from Bridgetown, Barbados to Genoa, Italy
Bridgetown, Barbados · Castries, St. Lucia · … · Genoa, Italy13 ports
Bridgetown, Barbados · Castries, St. Lucia · Funchal, Madeira, Portugal · Portimao, Portugal · Lisbon, Portugal · Cadiz (Seville), Spain · Ceuta, Spain · Motril, Spain · Cartagena, Spain · Sete, France · Marseille, France · Ajaccio, Corsica, France · Genoa, Italy
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPico do Arieiro to Pico RuivoSintra +6 more
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from $11,999
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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
Book This Cruise@ Cruisebound
Seabourn · Seabourn VentureOne-way
Caribbean 8 nights Oct 1 – Oct 9, 2027 from Halifax, Nova Scotia to Bridgetown, Barbados
Halifax, Nova Scotia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Little Bay, Montserrat, Leeward Islands · Rodney Bay, St. Lucia · Bridgetown, Barbados
★ Bucket-list Peggy's Cove & LunenburgMt. Liamuiga Volcano Crater HikeSwim with wild green sea turtles + two shipwrecks…
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from $5,998
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Nov 27 – Dec 4, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +1 more
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from $4,498
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 17 nights Dec 11 – Dec 28, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten15 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Scarborough, Tobago · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port Elizabeth, Saint Vincent · Saint-Pierre, Newfoundland, Canada · Terre-de-haut, Guadeloupe · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Road Bay, Anguilla · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Full-Day Curaçao Island Tour with Local Ex…Klein BonaireGrenada Private Taxi Tour +4 more
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from $8,998
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
Caribbean 14 nights Jan 8 – Jan 22, 2028 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Philipsburg, St. Maarten12 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Full-Day Curaçao Island Tour with Local Ex…ArubaKlein Bonaire +4 more
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from $8,898
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Jan 15 – Jan 29, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +3 more
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from $9,198
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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
Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Jan 29 – Feb 5, 2028 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · Castries, St. Lucia · … · Philipsburg, St. Maarten7 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +1 more
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from $4,798
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Feb 5 – Feb 19, 2028 from Philipsburg, St. Maarten
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Philipsburg, St. Maarten13 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeSchotia Private Game ReserveGrenada Private Taxi Tour +3 more
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from $8,898
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
Caribbean 14 nights Feb 12 – Feb 26, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados13 ports
Bridgetown, Barbados · Castries, St. Lucia · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Trois Ilets, Martinique · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater Hike +3 more
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from $9,498
Book This Cruise@ Cruisebound
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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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