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 Regent ×Visits Royal Naval Dockyard × Clear all
Showing 7 of 7 sailings
Regent · Seven Seas GrandeurOne-way
Bermuda 21 nights Nov 1 – Nov 22, 2026 from Piraeus (Athens), Greece to Miami, Florida
Piraeus (Athens), Greece · Mykonos, Greece · … · Miami, Florida16 ports
Piraeus (Athens), Greece · Mykonos, Greece · Katakolon (Olympia), Greece · Willis Island · Valletta, Malta · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy · Willis Island · Palma de Mallorca, Spain · Willis Island · Funchal, Madeira, Portugal · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Miami, Florida
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineDelosAncient OlympiaZodiac Circumnavigation of Willis Island +8 more
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from $14,205
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Regent · Seven Seas GrandeurOne-way
Bermuda 21 nights Nov 8 – Nov 29, 2026 from Civitavecchia (Rome), Italy to Miami, Florida
Civitavecchia (Rome), Italy · Willis Island · … · Miami, Florida16 ports
Civitavecchia (Rome), Italy · Willis Island · Palma de Mallorca, Spain · Willis Island · Funchal, Madeira, Portugal · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Miami, Florida · Willis Island · Roatan, Honduras · Santo Tomas de Castilla, Guatemala · Harvest Caye, Belize · Costa Maya, Mexico · Willis Island · Miami, Florida
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayZodiac Circumnavigation of Willis IslandLa Seu Cathedral + Rooftop Terraces ClimbPico do Arieiro to Pico Ruivo +5 more
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from $14,399
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Regent · Seven Seas PrestigeOne-way
Bermuda 14 nights Apr 9 – Apr 23, 2027 from Miami, Florida to New York, New York
Miami, Florida · Willis Island · … · New York, New York13 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · San Juan, Puerto Rico · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · New York, New York
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +6 more
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from $10,199
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Regent · Seven Seas GrandeurOne-way
Bermuda 24 nights Apr 14 – May 8, 2027 from Miami, Florida to Lisbon, Portugal
Miami, Florida · Willis Island · … · Lisbon, Portugal15 ports
Miami, Florida · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Ponta Delgada, Azores, Portugal · Willis Island · Malaga, Spain · Cadiz (Seville), Spain · Lisbon, Portugal · Willis Island · Santander, Spain · Bordeaux, France · Bilbao, Spain · Willis Island · Lisbon, Portugal
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Island Wrap-Around Van Tour of BermudaGranada & the Alhambra +3 more
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from $15,699
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Regent · Seven Seas PrestigeOne-way
Caribbean 14 nights Apr 27 – May 11, 2027 from New York, New York to Barcelona, Spain
New York, New York · Willis Island · … · Barcelona, Spain12 ports
New York, New York · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Horta, Azores, Portugal · Willis Island · Funchal, Madeira, Portugal · Willis Island · Malaga, Spain · Cartagena, Colombia · Valencia, Spain · Barcelona, Spain
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPrivate Island Wrap-Around Van Tour of BermudaPico do Arieiro to Pico Ruivo +4 more
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from $10,549
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Regent · Seven Seas VoyagerOne-way
Bermuda 14 nights Mar 18 – Apr 1, 2028 from Miami, Florida to Barcelona, Spain
Miami, Florida · Willis Island · … · Barcelona, Spain10 ports
Miami, Florida · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Horta, Azores, Portugal · Willis Island · Cadiz (Seville), Spain · Willis Island · Valencia, Spain · Barcelona, Spain
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Island Wrap-Around Van Tour of BermudaReal Alcázar de Sevilla +2 more
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from $5,799
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Regent · Seven Seas PrestigeOne-way
Bermuda 14 nights Mar 26 – Apr 9, 2028 from Miami, Florida to Lisbon, Portugal
Miami, Florida · Willis Island · … · Lisbon, Portugal10 ports
Miami, Florida · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Ponta Delgada, Azores, Portugal · Willis Island · Funchal, Madeira, Portugal · Willis Island · Cadiz (Seville), Spain · Lisbon, Portugal
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Island Wrap-Around Van Tour of BermudaPico do Arieiro to Pico Ruivo +2 more
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from $9,699
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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