Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

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 Australia & South Pacific ×Bahamas ×From San Juan, Puerto Rico × Clear all
Showing 9 of 9 sailings
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 WallsPrivate Open-Top Mini Moke Island Tour of St. BartsRandom Wind 'Paradise Day Sail'Mt. Liamuiga Volcano Crater Hike +3 more
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from $2,970
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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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Princess · Crown PrincessOne-way
Caribbean 7 nights Mar 28 – Apr 4, 2027 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachArubaKlein Curaçao Private Day Trip +1 more
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from $514
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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 +7 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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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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Disney · Disney DreamOne-way
Bahamas 4 nights Apr 23 – Apr 27, 2027 from San Juan, Puerto Rico to Port Canaveral, Florida
San Juan, Puerto Rico · Disney Lookout Cay · Castaway Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Historical & Cultural SUV Tour of EleutheraAbaco Backcountry Fishing AdventureKennedy Space Center Visitor Complex
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from $1,509
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Celebrity · Celebrity SummitOne-way
Caribbean 4 nights Jan 2 – Jan 6, 2028 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · Philipsburg, St. Maarten · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Everglades Airboat Skim + Gator Boys Live Show
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from $506
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Princess · Emerald PrincessOne-way
Caribbean 7 nights Mar 26 – Apr 2, 2028 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · Curacao, Caribbean · Port of Oranjestad, Aruba, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsKlein Curaçao Private Day TripArubaKlein Bonaire +1 more
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from $634
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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