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 1 selected · clear 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
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines · 1 selected
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 Caribbean ×Viking Ocean ×13+ nights × Clear all
Showing 5 of 5 sailings
Viking Ocean · Viking SeaRepositioning
Caribbean 20 nights Oct 16 – Nov 5, 2026 from Civitavecchia (Rome), Italy to San Juan, Puerto Rico
Civitavecchia (Rome), Italy · Florence, Italy · … · San Juan, Puerto Rico13 ports
Civitavecchia (Rome), Italy · Florence, Italy · Monte Carlo, Monaco · Marseille, France · Sete, France · Barcelona, Spain · Valencia, Spain · Sail the Alboran Sea · Sail the Atlantic Ocean · Funchal, Madeira, Portugal · Sail the Atlantic Ocean · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayUffizi GalleryCasino de Monte-CarloCalanques National Park Boat Cruise from the Old P… +6 more
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from $7,398
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Viking Ocean · Viking SeaRepositioning
Caribbean 13 nights Oct 23 – Nov 5, 2026 from Barcelona, Spain to San Juan, Puerto Rico
Barcelona, Spain · Valencia, Spain · … · San Juan, Puerto Rico8 ports
Barcelona, Spain · Valencia, Spain · Sail the Alboran Sea · Sail the Atlantic Ocean · Funchal, Madeira, Portugal · Sail the Atlantic Ocean · Philipsburg, St. Maarten · San Juan, Puerto Rico
★ Bucket-list Sagrada FamiliaOceanograficPico do Arieiro to Pico RuivoRandom Wind 'Paradise Day Sail' +1 more
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from $3,299
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Viking Ocean · Viking SeaRound-trip
Caribbean 21 nights Dec 15 – Jan 5, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Sail the Caribbean Sea · … · San Juan, Puerto Rico18 ports
San Juan, Puerto Rico · Sail the Caribbean Sea · Bridgetown, Barbados · Sail the Caribbean Sea · Iles du Salut, Guiana · Sail the Atlantic Ocean · Sail The Amazon River · Santarem, Brazil · Parintins, Brazil · Manaus, Brazil · Sail the Amazon River · Belem, Brazil · Sail the Atlantic Ocean · Scarborough, Tobago · Castries, St. Lucia · St. John's, Antigua · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsSwim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $12,499
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Viking Ocean · Viking SeaRepositioning
Mediterranean 13 nights Mar 6 – Mar 19, 2027 from San Juan, Puerto Rico to Barcelona, Spain
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · Barcelona, Spain9 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Sail the Atlantic Ocean · Funchal, Madeira, Portugal · Sail the Atlantic Ocean · Cadiz (Seville), Spain · Sail the Alboran Sea · Valencia, Spain · Barcelona, Spain
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Pico do Arieiro to Pico RuivoReal Alcázar de Sevilla +2 more
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from $3,499
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Viking Ocean · Viking SeaRound-trip
Caribbean 21 nights Jan 6 – Jan 27, 2028 from San Juan, Puerto Rico
San Juan, Puerto Rico · Sail the Caribbean Sea · … · San Juan, Puerto Rico18 ports
San Juan, Puerto Rico · Sail the Caribbean Sea · Bridgetown, Barbados · Sail the Atlantic Ocean · Iles du Salut, Guiana · Sail the Atlantic Ocean · Sail The Amazon River · Santarem, Brazil · Parintins, Brazil · Manaus, Brazil · Sail the Amazon River · Belem, Brazil · Sail the Atlantic Ocean · Scarborough, Tobago · Castries, St. Lucia · St. John's, Antigua · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsSwim with wild green sea turtles + two shipwrecks…Cosol ToursPrivate Half-Day Island Adventure & Trunk Bay Beach +1 more
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from $23,599
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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