Bucket-List Cruise Adventures

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Filtering Caribbean ×Virgin Voyages ×Oceania × Clear all
Showing 36 of 56 sailings
Virgin Voyages · Valiant LadyOne-way
Bermuda Oct 19, 2026 from Brooklyn, NY to San Juan, Puerto Rico
Brooklyn, NY · Kings Wharf, Bermuda · … · San Juan, Puerto Rico7 ports
Brooklyn, NY · Kings Wharf, Bermuda · Bimini, Bahamas · St. Croix, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Swim with Wild Dolphins at Honeymoon HarbourBuck Island ReefMaho BeachNorman Island +1 more
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from $1,443
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Oct 31, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Willemstad, Curacao · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · 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 WallsPrivate Full-Day Curaçao Island Tour with Local Ex…ArubaMount Pelée & Saint-Pierre +1 more
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from $1,253
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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 Nov 20, 2026 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 · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · 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…Private Full-Day Curaçao Island Tour with Local Ex…Aruba +2 more
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from $1,437
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 28, 2026 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 · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · 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…Norman IslandMt. Liamuiga Volcano Crater Hike +2 more
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from $1,273
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 5, 2026 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 · Willemstad, Curacao · 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 WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,253
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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 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeMount Pelée & Saint-PierreAruba +1 more
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from $1,183
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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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Oceania · Oceania MarinaOne-way
Caribbean 10 nights Jan 5 – Jan 15, 2027 from Miami, Florida to Panama City, Panama
Miami, Florida · Cozumel, Mexico · … · Panama City, Panama10 ports
Miami, Florida · Cozumel, Mexico · Costa Maya, Mexico · Harvest Caye, Belize · Santo Tomas de Castilla, Guatemala · Roatan, Honduras · Puerto Limon, Costa Rica · Panama City, Panama · Kiel Canal, Germany · Panama City, Panama
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…El Cielo + Palancar + Columbia 3-Stop SnorkelChacchoben Mayan RuinsLamanai Mayan Ruins +1 more
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from $2,760
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 9, 2027 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 · Willemstad, Curacao · 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 WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,190
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Oceania · Oceania MarinaOne-way
Panama Canal 10 nights Jan 15 – Jan 25, 2027 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida9 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Colombia · Santa Marta, Colombia · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida
★ Bucket-list The Roman Theatre of Cartagena with the Rafael Mon…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Blue Hole & Secret Falls +2 more
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from $5,099
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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 Jan 29, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Fort-de-France, Martinique · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +2 more
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from $1,519
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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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Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 6, 2027 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 · Willemstad, Curacao · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Private Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $1,063
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 13, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Samana, Dominican Republic · Grand Turk, Turks and Caicos · Cabo Rojo, Dominican Republic · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGibbs Cay Private Stingray Swim & Reef Snorkel
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from $1,966
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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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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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Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 27, 2027 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 · Willemstad, Curacao · 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 WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,260
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Oceania · Oceania MarinaOne-way
Caribbean 10 nights Mar 5 – Mar 15, 2027 from Miami, Florida to Panama City, Panama
Miami, Florida · Cozumel, Mexico · … · Panama City, Panama10 ports
Miami, Florida · Cozumel, Mexico · Costa Maya, Mexico · Harvest Caye, Belize · Santo Tomas de Castilla, Guatemala · Roatan, Honduras · Puerto Limon, Costa Rica · Panama City, Panama · Kiel Canal, Germany · Panama City, Panama
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…El Cielo + Palancar + Columbia 3-Stop SnorkelChacchoben Mayan RuinsLamanai Mayan Ruins +1 more
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from $2,560
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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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Oceania · Oceania MarinaOne-way
Panama Canal 10 nights Mar 15 – Mar 25, 2027 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida9 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Colombia · Santa Marta, Colombia · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida
★ Bucket-list The Roman Theatre of Cartagena with the Rafael Mon…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Blue Hole & Secret Falls +2 more
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from $2,640
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Mar 19, 2027 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 · Port of Kingstown, St. Vincent & the Grenadines · Roseau, Dominica · 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…Boiling Lake Hike +1 more
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from $1,504
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Virgin Voyages · Valiant LadyRound-trip
Caribbean Apr 3, 2027 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 · Willemstad, Curacao · 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 WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
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from $1,258
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Virgin Voyages · Valiant LadyOne-way
Bahamas Apr 10, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Grand Turk, Turks and Caicos · Bimini, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsGibbs Cay Private Stingray Swim & Reef SnorkelSwim with Wild Dolphins at Honeymoon HarbourStar Island & Millionaire's Row Skyline Cruise on…
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from $922
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Virgin Voyages · Scarlet LadyRepositioning
Mediterranean Oct 31, 2027 from Barcelona, Spain to San Juan, Puerto Rico
Barcelona, Spain · Tangier, Morocco · Lanzarote, Canary Islands, Spain · San Juan, Puerto Rico
★ Bucket-list Sagrada FamiliaTangier Kasbah, Medina & American Legation Private…Walk El Morro & Old San Juan's City Walls
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from $1,415
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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 20, 2027 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 · Willemstad, Curacao · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Private Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $932
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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
View →
from $932
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Virgin Voyages · Scarlet LadyRound-trip
Caribbean Dec 4, 2027 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 · Willemstad, Curacao · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Private Half-Day Island Adventure & Trunk Bay Beach +1 more
View →
from $1,002
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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
View →
from $997
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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