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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Filtering Virgin Voyages ×Visits St. Thomas × Clear all

Showing 15 of 15 sailings

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 Walls Private 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 Walls Private Catamaran Sail & Snorkel at Honeymoon Beac…Norman Island Mt. Liamuiga Volcano Crater Hike +2 more

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from $1,273

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Virgin Voyages · Brilliant LadyRound-trip

Bahamas Dec 14, 2026 from Miami, Florida

Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida6 ports

Miami, Florida · St. Maarten, Netherlands Antilles · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Bimini, Bahamas · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Maho Beach Private Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls +1 more

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from $1,222

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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 Walls Private 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 · Brilliant LadyRound-trip

Bahamas Dec 14, 2027 from Miami, Florida

Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida6 ports

Miami, Florida · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Bimini, Bahamas · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City Walls Private Catamaran Sail & Snorkel at Honeymoon Beac…Maho Beach +1 more

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from $1,336

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Virgin Voyages · Scarlet LadyRound-trip

Caribbean Dec 26, 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 · Fort-de-France, Martinique · St. John's, Antigua · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more

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from $1,846

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Virgin Voyages · Brilliant LadyRound-trip

Caribbean Jan 10, 2028 from Miami, Florida

Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida8 ports

Miami, Florida · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Maho Beach Norman Island Private Catamaran Sail & Snorkel at Honeymoon Beac… +3 more

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from $1,573

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Virgin Voyages · Scarlet LadyRound-trip

Caribbean Jan 15, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Sail & Snorkel at Honeymoon Beac…Swim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay Beach +1 more

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from $980

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Virgin Voyages · Brilliant LadyRound-trip

Caribbean Jan 24, 2028 from Miami, Florida

Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida8 ports

Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Croix, U.S. Virgin Islands · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Maarten, Netherlands Antilles · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Buck Island Reef +3 more

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from $1,510

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Virgin Voyages · Scarlet LadyRound-trip

Caribbean Jan 29, 2028 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 · 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 Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more

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from $979

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Virgin Voyages · Brilliant LadyRound-trip

Caribbean Feb 7, 2028 from Miami, Florida

Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida8 ports

Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Maarten, Netherlands Antilles · Miami, Florida

★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua Waterfalls Walk El Morro & Old San Juan's City Walls Norman Island +3 more

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from $1,519

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Virgin Voyages · Scarlet LadyRound-trip

Caribbean Feb 12, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Sail & Snorkel at Honeymoon Beac…Swim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more

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from $1,057

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Virgin Voyages · Scarlet LadyRound-trip

Caribbean Feb 26, 2028 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 · 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 Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more

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from $1,056

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Virgin Voyages · Scarlet LadyRound-trip

Caribbean Mar 11, 2028 from San Juan, Puerto Rico

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports

San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Bridgetown, Barbados · Fort-de-France, Martinique · Roseau, Dominica · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico

★ Bucket-list Walk El Morro & Old San Juan's City Walls Private Catamaran Sail & Snorkel at Honeymoon Beac…Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more

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from $1,127

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Virgin Voyages · Scarlet LadyRound-trip

Caribbean Mar 25, 2028 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 · 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 Walk El Morro & Old San Juan's City Walls Maho Beach Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-Pierre +2 more

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from $1,119

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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