Bucket-List Cruise Adventures

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Showing 36 of 42 sailings
Windstar · Star PrideRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $2,411
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Windstar · Wind StarOne-way
Caribbean 11 nights Nov 24 – Dec 5, 2026 from Bridgetown, Barbados to Colon, Panama
Bridgetown, Barbados · Bequia, Grenadines · … · Colon, Panama9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Kralendijk, Bonaire · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cartagena, Colombia · San Blas Islands, Panama · Colon, Panama
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourKlein Bonaire +5 more
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from $7,896
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Windstar · Star LegendRound-trip
Mediterranean 7 nights Nov 27 – Dec 4, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Anses D'arlet, Martinique · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Anses D'arlet, Martinique · Rodney Bay, St. Lucia · Casablanca, Morocco · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Small-Boat Snorkel with Wild Sea Turtles, Anse NoireFull-Day Private Catamaran Sail to Soufrière & the…Private Guided Tour of Casablanca with Hassan II M… +3 more
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from $2,594
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Windstar · Star LegendOne-way
Caribbean 8 nights Dec 4 – Dec 12, 2026 from Bridgetown, Barbados to Port of Oranjestad, Aruba, Caribbean
Bridgetown, Barbados · Rodney Bay, St. Lucia · … · Port of Oranjestad, Aruba, Caribbean8 ports
Bridgetown, Barbados · Rodney Bay, St. Lucia · Sca · Bequia, Grenadines · Mayreau, Grenadines · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Full-Day Private Catamaran Sail to Soufrière & the…Tobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +3 more
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from $2,940
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Silversea · Silver SpiritRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Deshaies, Guadeloupe · Gustavia, St. Barts · Codrington, Barbuda · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierreJardin Botanique de Deshaies at Opening Hour +3 more
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from $4,550
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Windstar · Star PrideRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Deshaies, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $3,636
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Silversea · Silver SpiritRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Deshaies, Guadeloupe · Codrington, Barbuda · Iles des Saintes, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursMount Pelée & Saint-PierreJardin Botanique de Deshaies at Opening Hour +3 more
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from $4,450
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Silversea · Silver SpiritRound-trip
Caribbean 8 nights Dec 19 – Dec 27, 2026 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Cruz Bay, St. John, U.S. Virgin Islands · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierreBoiling Lake Hike +3 more
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from $3,650
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Silversea · Silver NovaOne-way
Caribbean 8 nights Dec 21 – Dec 29, 2026 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Soufriere, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Soufriere, St. Lucia · Bequia, Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourMount Pelée & Saint-Pierre +3 more
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from $4,050
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Silversea · Silver ShadowRound-trip
Caribbean 7 nights Dec 27 – Jan 3, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Iles des Saintes, Guadeloupe · Bequia, Grenadines · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikeSunrise Hike to Le Chameau's Summit Fort +2 more
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from $7,050
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Silversea · Silver SpiritRound-trip
Caribbean 8 nights Dec 27 – Jan 4, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Deshaies, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Georges, Grenada, West Indies · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierreJardin Botanique de Deshaies at Opening Hour +3 more
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from $5,750
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Windstar · Star PrideRound-trip
Caribbean 7 nights Jan 3 – Jan 10, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Deshaies, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +2 more
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from $4,896
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Silversea · Silver SpiritRound-trip
Caribbean 11 nights Jan 4 – Jan 15, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados10 ports
Bridgetown, Barbados · Castries, St. Lucia · Deshaies, Guadeloupe · Codrington, Barbuda · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursJardin Botanique de Deshaies at Opening HourBarbuda's Pink Sand Beach at Dawn, Private & Empty +5 more
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from $4,850
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Silversea · Silver SpiritRound-trip
Caribbean 10 nights Jan 15 – Jan 25, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourAruba +4 more
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from $4,950
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Silversea · Silver ShadowOne-way
Caribbean 10 nights Jan 20 – Jan 30, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Bequia, Grenadines · … · San Juan, Puerto Rico11 ports
Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Trois Ilets · Roseau, Dominica · Iles des Saintes, Guadeloupe · Little Bay, Montserrat, Leeward Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailCosol ToursLa Savane des Esclaves +7 more
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from $7,150
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Silversea · Silver SpiritOne-way
Caribbean 12 nights Jan 25 – Feb 6, 2027 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Bequia, Grenadines · … · Miami, Florida9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourKlein Bonaire +5 more
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from $4,250
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Silversea · Silver RayOne-way
Caribbean 12 nights Feb 7 – Feb 19, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados11 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Codrington, Barbuda · Deshaies, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater Hike +7 more
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from $9,200
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Silversea · Silver ShadowOne-way
Caribbean 10 nights Feb 16 – Feb 26, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Bequia, Grenadines · … · San Juan, Puerto Rico11 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Castries, St. Lucia · Trois Ilets · Roseau, Dominica · Iles des Saintes, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Jost Van Dyke, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourCosol Tours +7 more
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from $7,450
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Explora Journeys · EXPLORA IOne-way
Caribbean 19 nights Feb 17, 2027 from Manaus, Brazil to Miami, Florida
Manaus, Brazil · Parintins, Brazil · … · Miami, Florida16 ports
Manaus, Brazil · Parintins, Brazil · Alter Do Chão · Macapa, Brazil · Devils Island, French Guiana · Bequia, Grenadines · Bridgetown, Barbados · Castries, St. Lucia · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · St. John's, Antigua · Road Bay, Anguilla · Virgin Gorda, British Virgin Islands · Grand Turk, Turks and Caicos · Miami, Florida
★ Bucket-list Meeting of the WatersÎles du SalutTobago Cays & Mystique Full-Day Private SailSwim with wild green sea turtles + two shipwrecks… +9 more
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from $11,865
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Silversea · Silver SpiritRound-trip
Caribbean 10 nights Feb 18 – Feb 28, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourKlein Bonaire +4 more
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from $6,250
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Silversea · Silver RayOne-way
Caribbean 12 nights Feb 26 – Mar 10, 2027 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Bequia, Grenadines · … · Miami, Florida11 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Fort-de-France, Martinique · Deshaies, Guadeloupe · Soufriere, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · Anguilla, Caribbean · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourMount Pelée & Saint-Pierre +6 more
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from $8,900
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Silversea · Silver SpiritRound-trip
Caribbean 7 nights Feb 28 – Mar 7, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Castries, St. Lucia · Gustavia, St. Barts · Cruz Bay, St. John, U.S. Virgin Islands · Codrington, Barbuda · Roseau, Dominica · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Open-Top Mini Moke Island Tour of St. BartsTrunk Bay Underwater Snorkel Trail & VI National P… +3 more
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from $5,150
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Explora Journeys · EXPLORA IIIOne-way
Caribbean 7 nights Mar 7, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · Bridgetown, Barbados11 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Grand Turk, Turks and Caicos · Miami, Florida · Providenciales, Turks & Caicos · St. John's, Antigua · Pointe-a-Pitre, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. BartsMt. Liamuiga Volcano Crater Hike +7 more
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from $8,680
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Silversea · Silver SpiritOne-way
Caribbean 12 nights Mar 7 – Mar 19, 2027 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Bequia, Grenadines · … · Miami, Florida9 ports
Bridgetown, Barbados · Bequia, Grenadines · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Spanish Town · San Juan, Puerto Rico · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailGrenada Private Taxi TourPrivate Full-Day Curaçao Island Tour with Local Ex… +4 more
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from $6,800
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 15 nights Mar 14, 2027 from Miami, Florida
Miami, Florida · Providenciales, Turks & Caicos · … · Miami, Florida12 ports
Miami, Florida · Providenciales, Turks & Caicos · St. John's, Antigua · Pointe-a-Pitre, Guadeloupe · Bequia, Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Castries, St. Lucia · Martinique/fort De France · Gustavia, St. Barts · Virgin Gorda, British Virgin Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefPrivate Half-Day Island Adventure & Trunk Bay BeachDeath in Paradise Filming Locations & Botanical Ga… +6 more
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from $10,185
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Silversea · Silver SpiritOne-way
Caribbean 12 nights Mar 19 – Mar 31, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · San Juan, Puerto Rico · … · Bridgetown, Barbados9 ports
Miami, Florida · San Juan, Puerto Rico · Cruz Bay, St. John, U.S. Virgin Islands · Gustavia, St. Barts · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Bequia, Grenadines · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Private Open-Top Mini Moke Island Tour of St. Barts +5 more
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from $6,800
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Windstar · Star PrideRound-trip
Mediterranean 14 nights Nov 1 – Nov 15, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Cruz Bay, St. John · … · San Juan, Puerto Rico14 ports
San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTrunk Bay Underwater Snorkel Trail & VI National P…Mt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +8 more
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from $3,902
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Windstar · Star PrideRound-trip
Mediterranean 14 nights Nov 8 – Nov 22, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · … · San Juan, Puerto Rico14 ports
San Juan, Puerto Rico · St. Georges, Grenada, West Indies · Bequia, Grenadines · Mayreau, Grenadines · Les Saintes, Guadeloupe · Marmaris, Turkey · San Juan, Puerto Rico · Cruz Bay, St. John · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Philipsburg, St. Maarten · Jost Van Dyke, British Virgin Islands · Virgin Gorda, British Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailSalt Whistle Bay +8 more
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from $4,084
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Silversea · Silver DawnRound-trip
Caribbean 10 nights Dec 11 – Dec 21, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · … · San Juan, Puerto Rico11 ports
San Juan, Puerto Rico · Jost Van Dyke, British Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Bequia, Grenadines · Castries, St. Lucia · Codrington, Barbuda · Cruz Bay, St. John, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran CharterMt. Liamuiga Volcano Crater HikePrivate Open-Top Mini Moke Island Tour of St. Barts +6 more
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from $6,050
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Silversea · Silver SpiritRound-trip
Caribbean 11 nights Dec 17 – Dec 28, 2027 from Bridgetown, Barbados
Bridgetown, Barbados · Castries, St. Lucia · … · Bridgetown, Barbados10 ports
Bridgetown, Barbados · Castries, St. Lucia · Bequia, Grenadines · St. Georges, Grenada, West Indies · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursTobago Cays & Mystique Full-Day Private SailGrenada Private Taxi Tour +5 more
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from $6,450
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Silversea · Silver RayOne-way
Caribbean 8 nights Dec 18 – Dec 26, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Castries, St. Lucia · … · San Juan, Puerto Rico8 ports
Bridgetown, Barbados · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bequia, Grenadines · Fort-de-France, Martinique · Roseau, Dominica · Codrington, Barbuda · San Juan, Puerto Rico
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Cosol ToursGrenada Private Taxi TourTobago Cays & Mystique Full-Day Private Sail +4 more
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from $5,950
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Silversea · Silver SpiritRound-trip
Caribbean 13 nights Dec 28 – Jan 10, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados12 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Bequia, Grenadines · Castries, St. Lucia · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · Codrington, Barbuda · Fort-de-France, Martinique · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourTobago Cays & Mystique Full-Day Private SailCosol Tours +7 more
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from $7,550
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Silversea · Silver SpiritRound-trip
Caribbean 12 nights Jan 10 – Jan 22, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · Bequia, Grenadines · Castries, St. Lucia · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailCosol ToursKlein Bonaire +6 more
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from $6,550
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Explora Journeys · EXPLORA IIRound-trip
Caribbean 7 nights Jan 16, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Bequia, Grenadines · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Bequia, Grenadines · Castries, St. Lucia · Bridgetown, Barbados · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsTobago Cays & Mystique Full-Day Private SailCosol ToursSwim with wild green sea turtles + two shipwrecks… +2 more
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from $4,020
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Silversea · Silver SpiritRound-trip
Caribbean 7 nights Jan 22 – Jan 29, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Gustavia, St. Barts · Roseau, Dominica · St. Georges, Grenada, West Indies · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierrePrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $4,950
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Silversea · Silver SpiritRound-trip
Caribbean 7 nights Jan 29 – Feb 5, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · Bequia, Grenadines · … · Bridgetown, Barbados8 ports
Bridgetown, Barbados · Bequia, Grenadines · Fort-de-France, Martinique · Gustavia, St. Barts · Roseau, Dominica · St. Georges, Grenada, West Indies · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Tobago Cays & Mystique Full-Day Private SailMount Pelée & Saint-PierrePrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $4,950
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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 Norwegian AmaWaterways Costa Princess Celebrity Avalon Disney Viking Ocean Holland America Silversea Oceania Virgin Regent Explora Journeys Cunard Azamara Windstar Seabourn Virgin Voyages