Bucket-List Cruise Adventures

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Showing 36 of 150 sailings
Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Sep 18 – Sep 26, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexBuck Island ReefPrivate Full-Day Boat CharterWalk El Morro & Old San Juan's City Walls +1 more
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from $1,232
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Sep 26 – Oct 3, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
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from $606
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 3 – Oct 10, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $583
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 10 – Oct 17, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
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from $606
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Royal Caribbean · Adventure of the SeasRound-trip
Caribbean 8 nights Oct 16 – Oct 24, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · … · Port Canaveral, Florida6 ports
Port Canaveral, Florida · St. Croix, U.S. Virgin Islands · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Perfect Day at CocoCay · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexBuck Island ReefPrivate Full-Day Boat CharterWalk El Morro & Old San Juan's City Walls +1 more
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from $1,592
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Carnival · Carnival DreamRound-trip
Caribbean 14 nights Oct 17, 2026 from Galveston, Texas
Galveston, Texas · Key West, Florida · … · Galveston, Texas10 ports
Galveston, Texas · Key West, Florida · Grand Turk, Turks and Caicos · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Ocho Rios, Jamaica · Galveston, Texas
★ Bucket-list Moody GardensDry Tortugas National ParkGibbs Cay Private Stingray Swim & Reef SnorkelWalk El Morro & Old San Juan's City Walls +5 more
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from $1,110
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Virgin · Valiant LadyOne-way
Bermuda 12 nights 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 NYC Private VIP Tour by VehicleDolphin QuestSwim with Wild Dolphins at Honeymoon HarbourBuck Island Reef +3 more
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from $1,188
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 24 – Oct 31, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
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from $563
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Oct 31 – Nov 7, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $722
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 1 – Nov 8, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · 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 Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $726
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 5 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $5,399
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $684
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Nov 8, 2026 from Miami, Florida
Miami, Florida · Providenciales, Turks & Caicos · … · Miami, Florida13 ports
Miami, Florida · Providenciales, Turks & Caicos · Puerto Plata, Dominican Republic · La Romana, Dominican Republic · Jost Van Dyke, British Virgin Islands · Gustavia, St. Barts · San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Iguana Island & ReefThe full 27 jumps at the Damajagua WaterfallsSaona Island Private Speedboat & Natural Pool Day +6 more
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from $8,735
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $549
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 14 – Nov 21, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay BeachBoiling Lake Hike +2 more
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from $578
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Explora Journeys · EXPLORA IIIRound-trip
Caribbean 7 nights Nov 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Island HoppingPrivate Half-Day Island Adventure & Trunk Bay BeachPrivate Pyramids of Giza, Sphinx & Grand Egyptian… +4 more
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from $10,200
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · 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 Boat CharterPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $548
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 15 – Nov 25, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $4,999
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $836
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 22 – Nov 29, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $856
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Nov 25 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $4,999
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
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from $531
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Regent · Seven Seas GrandeurRound-trip
Bahamas 10 nights Nov 29 – Dec 9, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandWalk El Morro & Old San Juan's City WallsPrivate Open-Top Mini Moke Island Tour of St. Barts +3 more
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from $6,949
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $542
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Virgin · Brilliant LadyRound-trip
Caribbean 10 nights Nov 30, 2026 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. Croix, 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 BeachNorman IslandBuck Island Reef +3 more
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from $1,190
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Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Dec 2 – Dec 12, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterPrivate Open-Top Mini Moke Island Tour of St. BartsRandom Wind 'Paradise Day Sail' +1 more
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from $4,095
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $519
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Viking Ocean · Viking SeaRound-trip
Caribbean 10 nights Dec 5 – Dec 15, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeCosol Tours +5 more
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from $5,599
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Virgin · Resilient LadyRound-trip
Caribbean 8 nights Dec 5, 2026 from Miami, Florida
Miami, Florida · St. Croix, U.S. Virgin Islands · … · Miami, Florida6 ports
Miami, Florida · St. Croix, 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…Buck Island ReefWalk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $792
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail' +2 more
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from $611
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
★ 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 +2 more
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from $666
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Dec 13 – Dec 20, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $621
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Royal Caribbean · Rhapsody of the SeasRound-trip
Caribbean 7 nights Dec 19 – Dec 26, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 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 · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefRandom Wind 'Paradise Day Sail' +2 more
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from $846
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Dec 20 – Dec 27, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachBoiling Lake Hike +2 more
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from $714
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Royal Caribbean · Vision of the SeasRound-trip
Caribbean 7 nights Dec 27 – Jan 3, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · St. John's, Antigua · Roseau, Dominica · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterBuck Island ReefPrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $1,487
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Azamara · Azamara JourneyOne-way
Caribbean 8 nights Dec 28 – Jan 5, 2027 from Bridgetown, Barbados to San Juan, Puerto Rico
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico7 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
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Cosol Tours +2 more
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from $1,929
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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