Bucket-List Cruise Adventures

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Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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Filtering Caribbean ×Regent ×From Miami, Florida × Clear all
Showing 7 of 7 sailings
Regent · Seven Seas SplendorOne-way
Mexico 15 nights Nov 15 – Nov 30, 2026 from Miami, Florida to Galveston, Texas
Miami, Florida · Willis Island · … · Galveston, Texas15 ports
Miami, Florida · Willis Island · Willemstad, Curacao · Oranjestad, Sint Eustatius · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Roatan, Honduras · Willis Island · Cozumel, Mexico · Progresso, Mexico · Willis Island · Galveston, Texas
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Curaçao Island Tour with Local Ex…The Natural Pool +7 more
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from $9,799
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Regent · Seven Seas MarinerOne-way
Caribbean 10 nights Dec 1 – Dec 11, 2026 from Miami, Florida to Tampa, Florida
Miami, Florida · Willis Island · … · Tampa, Florida10 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Tampa, Florida
★ 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… +4 more
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from $7,900
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Regent · Seven Seas SplendorOne-way
Mediterranean 14 nights Jan 12 – Jan 26, 2027 from Miami, Florida to Panama City, Panama
Miami, Florida · Willis Island · … · Panama City, Panama15 ports
Miami, Florida · Willis Island · Cozumel, Mexico · Costa Maya, Mexico · Harvest Caye, Belize · Roatan, Honduras · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Willis Island · Puerto Limon, Costa Rica · Willis Island · Cartagena, Spain · Panama Canal, Panama · Panama City, Panama
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandEl Cielo + Palancar + Columbia 3-Stop SnorkelChacchoben Mayan Ruins +8 more
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from $14,099
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Regent · Seven Seas GrandeurOne-way
Mediterranean 14 nights Feb 23 – Mar 9, 2027 from Miami, Florida to Panama City, Panama
Miami, Florida · Willis Island · … · Panama City, Panama15 ports
Miami, Florida · Willis Island · Costa Maya, Mexico · Harvest Caye, Belize · Roatan, Honduras · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Willis Island · Puerto Limon, Costa Rica · Willis Island · Cartagena, Spain · Colon, Panama · Panama Canal, Panama · Panama City, Panama
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandChacchoben Mayan RuinsLamanai Mayan Ruins +8 more
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from $9,299
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Regent · Seven Seas PrestigeOne-way
Caribbean 10 nights Mar 20 – Mar 30, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Willis Island · … · San Juan, Puerto Rico10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Boat CharterBoiling Lake Hike +6 more
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from $6,099
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Regent · Seven Seas GrandeurOne-way
Caribbean 10 nights Jan 5 – Jan 15, 2028 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Willis Island · … · Bridgetown, Barbados10 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Philipsburg, St. Maarten · Pointe-a-Pitre, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykePrivate Open-Top Mini Moke Island Tour of St. Barts +6 more
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from $6,399
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Regent · Seven Seas PrestigeOne-way
Mediterranean 12 nights Mar 2 – Mar 14, 2028 from Miami, Florida to Panama City, Panama
Miami, Florida · Key West, Florida · … · Panama City, Panama13 ports
Miami, Florida · Key West, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Falmouth, Jamaica · Willis Island · Cabo Rojo, Dominican Republic · Willis Island · Cartagena, Spain · Willis Island · Puerto Limon, Costa Rica · Kiel Canal, Germany · Panama City, Panama
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkZodiac Circumnavigation of Willis IslandStingray City Sandbar +6 more
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from $8,799
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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