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 2 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
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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 South America ×Caribbean ×Visits Monte Carlo × Clear all
Showing 2 of 2 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 JupiterRepositioning
Mediterranean 28 nights Nov 6 – Dec 4, 2027 from Civitavecchia (Rome), Italy to Buenos Aires, Argentina
Civitavecchia (Rome), Italy · Florence, Italy · … · Buenos Aires, Argentina18 ports
Civitavecchia (Rome), Italy · Florence, Italy · Monte Carlo, Monaco · Marseille, France · Sete, France · Barcelona, Spain · Sail the Mediterranean Sea · Malaga, Spain · Casablanca, Morocco · Sail the Atlantic Ocean · Sao Vicente Island (mindelo) · Sail the Atlantic Ocean · Recife, Brazil · Sail the Atlantic Ocean · Rio de Janeiro, Brazil · Sail the Atlantic Ocean · Montevideo, Uruguay · Buenos Aires, Argentina
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayUffizi GalleryCasino de Monte-CarloCalanques National Park Boat Cruise from the Old P… +7 more
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from $9,998
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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