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
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
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Luxury Azamara Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering From San Juan, Puerto Rico ×One-way ×6–8 nights × Clear all
Showing 6 of 6 sailings
Azamara · Azamara JourneyOne-way
Caribbean 7 nights Nov 7 – Nov 14, 2026 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachÎle aux Marins +4 more
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from $2,059
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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 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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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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Royal Caribbean · Grandeur of the SeasOne-way
Panama Canal 7 nights Nov 27 – Dec 4, 2027 from San Juan, Puerto Rico to Colon, Panama
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Colon, Panama6 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Castries, St. Lucia · Willemstad, Curacao · Colon, Panama
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Cosol Tours +2 more
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from $597
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Azamara · Azamara QuestOne-way
Northern Europe 8 nights Dec 19 – Dec 27, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · … · Bridgetown, Barbados8 ports
San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · St. John's, Antigua · Portsmouth, England · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Scarborough, Tobago · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsThe Baths National ParkPrivate Half-Day Island Adventure & Trunk Bay BeachStonehenge & Salisbury Cathedral +4 more
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from $3,086
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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.

19 lines
aboard
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