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.

When are you free? — only cruises that fit entirely inside your dates
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Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
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Luxury Azamara Explora Journeys Oceania Regent Seabourn Silversea Viking Ocean Windstar River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Showing 6 of 6 sailings
Seabourn · Seabourn QuestRound-trip
Caribbean 16 nights Dec 20 – Jan 5, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida13 ports
Miami, Florida · San Juan, Puerto Rico · Road Bay, Anguilla · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Marigot, Saint Martin · Terre-de-haut, Guadeloupe · Fort-de-France, Martinique · Rodney Bay, St. Lucia · Roseau, Dominica · Little Bay, Montserrat, Leeward Islands · St. John's, Antigua · Great Harbor, Peter Island, BVI · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Island HoppingMt. Liamuiga Volcano Crater Hike +8 more
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from $8,799
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IIOne-way
Caribbean 7 nights Dec 12, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Marigot Bay, St. Lucia · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Full-Day Boat Charter +2 more
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from $4,020
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Explora Journeys · EXPLORA IIOne-way
Caribbean 7 nights Jan 9, 2028 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ain Sokhna, Egypt · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Marigot Bay, St. Lucia · Saint John/cruz Bay · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsPrivate Pyramids of Giza, Sphinx & Grand Egyptian…Private Full-Day Boat Charter +1 more
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from $4,020
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IVOne-way
Caribbean 7 nights Mar 18, 2028 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Saint John/cruz Bay · … · Miami, Florida6 ports
San Juan, Puerto Rico · Saint John/cruz Bay · Pointe-a-Pitre, Guadeloupe · Marigot Bay, St. Lucia · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsDeath in Paradise Filming Locations & Botanical Ga…Shipwreck Snorkel SafariStar Island & Millionaire's Row Skyline Cruise on…
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from $4,020
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IVOne-way
Bahamas 7 nights Apr 15, 2028 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Saint John/cruz Bay · … · Miami, Florida6 ports
San Juan, Puerto Rico · Saint John/cruz Bay · Pointe-a-Pitre, Guadeloupe · Marigot Bay, St. Lucia · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsDeath in Paradise Filming Locations & Botanical Ga…Shipwreck Snorkel SafariStar Island & Millionaire's Row Skyline Cruise on…
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from $3,755
Book This Cruise@ Cruisebound
Explora Journeys · EXPLORA IVOne-way
Caribbean 7 nights Apr 29, 2028 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Saint John/cruz Bay · … · Miami, Florida6 ports
San Juan, Puerto Rico · Saint John/cruz Bay · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Marigot Bay, St. Lucia · Miami, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsDeath in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeStar Island & Millionaire's Row Skyline Cruise on…
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from $3,755
Book This Cruise@ Cruisebound

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