Bucket-List Cruise Adventures

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Showing 30 of 30 sailings
Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Oct 22 – Nov 1, 2026 from Baltimore, Maryland to San Juan, Puerto Rico
Baltimore, Maryland · Grand Turk, Turks and Caicos · … · San Juan, Puerto Rico8 ports
Baltimore, Maryland · Grand Turk, Turks and Caicos · Philipsburg, St. Maarten · Roseau, Dominica · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Gibbs Cay Private Stingray Swim & Reef SnorkelRandom Wind 'Paradise Day Sail'Boiling Lake HikeMount Pelée & Saint-Pierre +3 more
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from $916
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Azamara · Azamara JourneyOne-way
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +2 more
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from $2,059
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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
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Costa · Costa FavolosaOne-way
Caribbean 7 nights Dec 16 – Dec 23, 2026 from Fort-de-France, Martinique to Fort-de-France, Martinique
Martinique Bay · Fort-de-France, Martinique · … · Fort-de-France, Martinique9 ports
Martinique Bay · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Sea Of Antilles Darkest Spot · Antigua, Antigua & Barbuda · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeAdventure Antigua +1 more
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from $1,097
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Princess · Crown PrincessOne-way
Caribbean 8 nights Dec 19 – Dec 27, 2026 from Fort Lauderdale (Port Everglades), Florida to San Juan, Puerto Rico
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Antigua, Antigua & Barbuda · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowArubaKlein Curaçao Private Day TripAdventure Antigua +2 more
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from $515
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Costa · Costa FascinosaOne-way
Caribbean 4 nights Dec 23 – Dec 27, 2026 from Pointe-a-Pitre, Guadeloupe to La Romana, Dominican Republic
Pointe-a-Pitre, Guadeloupe · Guadeloupe Bay · … · La Romana, Dominican Republic6 ports
Pointe-a-Pitre, Guadeloupe · Guadeloupe Bay · Antigua, Antigua & Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Adventure AntiguaMt. Liamuiga Volcano Crater HikeNorman Island +1 more
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from $723
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Azamara · Azamara JourneyOne-way
Caribbean 17 nights Dec 28 – Jan 14, 2027 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida14 ports
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Castries, St. Lucia · Port of Charlestown, Nevis, St. Kitts and Nevis · Frederikstad, St. Croix · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Cosol Tours +8 more
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from $7,329
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Azamara · Azamara JourneyOne-way
Caribbean 11 nights Jan 14 – Jan 25, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Saint John, New Brunswick · … · Bridgetown, Barbados10 ports
Miami, Florida · Saint John, New Brunswick · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Reversing Falls & Fundy Tidal BorePrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail' +5 more
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from $3,116
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Costa · Costa FavolosaOne-way
Caribbean 7 nights Feb 4 – Feb 11, 2027 from Fort-de-France, Martinique to Fort-de-France, Martinique
Martinique Bay · Fort-de-France, Martinique · … · Fort-de-France, Martinique9 ports
Martinique Bay · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Sea Of Antilles Darkest Spot · Philipsburg, St. Maarten · Santo Domingo, Dominican Republic · Antigua, Antigua & Barbuda · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail' +1 more
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from $1,037
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Oceania · Oceania AlluraOne-way
Caribbean 7 nights Feb 5 – Feb 12, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico6 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Gustavia, St. Barts · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $3,375
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Costa · Costa FavolosaOne-way
Caribbean 7 nights Feb 11 – Feb 18, 2027 from Fort-de-France, Martinique to Fort-de-France, Martinique
Martinique Bay · Fort-de-France, Martinique · … · Fort-de-France, Martinique9 ports
Martinique Bay · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Antigua, Antigua & Barbuda · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeNorman Island +1 more
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from $1,067
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Costa · Costa FavolosaOne-way
Caribbean 7 nights Feb 18 – Feb 25, 2027 from Fort-de-France, Martinique to Fort-de-France, Martinique
Martinique Bay · Fort-de-France, Martinique · … · Fort-de-France, Martinique9 ports
Martinique Bay · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Sea Of Antilles Darkest Spot · Road Town, Tortola, B.V.I. · Santo Domingo, Dominican Republic · Antigua, Antigua & Barbuda · Fort-de-France, Martinique
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeNorman Island +1 more
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from $1,067
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Oceania · Oceania AlluraOne-way
Caribbean 8 nights Feb 19 – Feb 27, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Gustavia, St. Barts · … · Miami, Florida7 ports
San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $2,970
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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
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Royal Caribbean · Rhapsody of the SeasOne-way
Caribbean 10 nights Mar 6 – Mar 16, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida9 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +5 more
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from $729
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MSC Cruises · MSC OperaOne-way
Caribbean 3 nights Mar 12 – Mar 15, 2027 from Fort-de-France, Martinique to La Romana, Dominican Republic
Fort-de-France, Martinique · St. John's, Antigua · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Mount Pelée & Saint-PierrePrivate Half-Day Island Adventure & Trunk Bay BeachNorman IslandSaona Island Private Speedboat & Natural Pool Day
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from $299
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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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Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Apr 4 – Apr 14, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +5 more
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from $792
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Royal Caribbean · Grandeur of the SeasOne-way
Caribbean 7 nights Apr 24 – May 1, 2027 from Colon, Panama to San Juan, Puerto Rico
Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · … · San Juan, Puerto Rico6 ports
Colon, Panama · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Panama Canal Full TransitLa Soufrière Volcano Summit HikeCosol ToursPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $539
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Azamara · Azamara QuestOne-way
Caribbean 17 nights Oct 28 – Nov 14, 2027 from New York, New York to Bridgetown, Barbados
New York, New York · Hamilton, Bermuda · … · Bridgetown, Barbados13 ports
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Manhattan Helicopter TourRandom Wind 'Paradise Day Sail'Norman IslandWalk El Morro & Old San Juan's City Walls +6 more
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from $5,583
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Norwegian · Norwegian PrimaOne-way
Caribbean 10 nights Nov 3 – Nov 13, 2027 from New York, New York to San Juan, Puerto Rico
New York, New York · Royal Naval Dockyard, Bermuda · … · San Juan, Puerto Rico9 ports
New York, New York · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. John's, Antigua · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaJost Van DykeMt. Liamuiga Volcano Crater Hike +5 more
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from $1,554
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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
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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
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Seabourn · Seabourn OvationOne-way
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Bridgetown, Barbados to Philipsburg, St. Maarten
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Philipsburg, St. Maarten10 ports
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…Grenada Private Taxi TourSchotia Private Game ReservePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $5,998
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Azamara · Azamara QuestOne-way
Northern Europe 8 nights Dec 19 – Dec 27, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Portsmouth, England · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachSchotia Private Game Reserve +2 more
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from $3,086
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Seabourn · Seabourn OvationOne-way
Caribbean 11 nights Dec 28 – Jan 8, 2028 from Philipsburg, St. Maarten to Bridgetown, Barbados
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · … · Bridgetown, Barbados10 ports
Philipsburg, St. Maarten · Sopers Hole, British Virgin Islands · Road Bay, Anguilla · Falmouth Harbour, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Terre-de-haut, Guadeloupe · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Bridgetown, Barbados
★ Bucket-list Random Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater HikeArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +2 more
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from $6,498
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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
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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
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Seabourn · Seabourn OvationOne-way
Caribbean 7 nights Mar 11 – Mar 18, 2028 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 · Great Harbor, Peter Island, BVI · Philipsburg, St. Maarten
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay BeachMt. Liamuiga Volcano Crater HikeRandom Wind 'Paradise Day Sail'
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from $4,798
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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