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.

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
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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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Showing 13 of 13 sailings
Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana
★ Bucket-list Private Luxury Boston TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Gros Piton Summit HikeGrenada Private Taxi Tour +4 more
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from $970
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Regent · Seven Seas MarinerRound-trip
Caribbean 22 nights Nov 9 – Dec 1, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida16 ports
Miami, Florida · Willis Island · Bridgetown, Barbados · Port of Spain, Trinidad · Willis Island · Santarem, Brazil · Boca da Valeria, Brazil · Manaus, Brazil · Parintins, Brazil · Alter do Chao, Brazil · Willis Island · St. Georges, Grenada, West Indies · Willis Island · San Juan, Puerto Rico · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandSwim with wild green sea turtles + two shipwrecks…Caroni Swamp +7 more
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from $15,099
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Regent · Seven Seas GrandeurRound-trip
Caribbean 22 nights Mar 9 – Mar 31, 2027 from Panama City, Panama
Panama City, Panama · Panama Canal, Panama · … · Panama City, Panama17 ports
Panama City, Panama · Panama Canal, Panama · Willis Island · Oranjestad, Sint Eustatius · Willis Island · Port of Spain, Trinidad · Willis Island · Manaus, Brazil · Boca da Valeria, Brazil · Alter do Chao, Brazil · Willis Island · St. Georges, Grenada, West Indies · Willis Island · Willemstad, Curacao · Willis Island · Panama Canal, Panama · Panama City, Panama
★ Bucket-list Panama Canal Miraflores LocksPanama Canal Full TransitZodiac Circumnavigation of Willis IslandThe Natural Pool +6 more
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from $20,949
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Regent · Seven Seas MarinerRound-trip
Australia & South Pacific 15 nights Mar 26 – Apr 10, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida15 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Fort-de-France, Martinique · Port of Kingstown, St. Vincent & the Grenadines · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Puerto Plata, Dominican Republic · Willis Island · Miami, Florida
★ 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 +7 more
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from $10,299
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Regent · Seven Seas GrandeurOne-way
Mediterranean 14 nights Mar 31 – Apr 14, 2027 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida14 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Santa Marta, Colombia · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
★ Bucket-list Panama Canal Miraflores LocksPrivate Expert Walking Tour of KielThe Roman Theatre of Cartagena with the Rafael Mon…Ciudad Perdida +9 more
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from $8,699
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Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Apr 4 – Apr 18, 2027 from New Orleans, Louisiana to Boston, Massachusetts
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · … · Boston, Massachusetts9 ports
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Tortola, B.V.I. · Boston, Massachusetts
★ Bucket-list Steamboat NatchezStingray City SandbarArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +5 more
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from $1,726
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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… +7 more
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from $10,199
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Regent · Seven Seas VoyagerRound-trip
Mediterranean 25 nights Dec 19 – Jan 13, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida26 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Oranjestad, Sint Eustatius · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Willis Island · Cartagena, Spain · Panama Canal, Panama · Colon, Panama · Puerto Limon, Costa Rica · Willis Island · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykePrivate Full-Day Boat Charter +17 more
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from $14,049
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Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Jan 15 – Jan 25, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Willis Island · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourLa Soufrière Volcano Summit HikeCosol Tours +6 more
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from $7,199
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Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Feb 4 – Feb 14, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourZodiac Circumnavigation of Willis IslandThe Natural Pool +5 more
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from $5,899
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Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Feb 14 – Feb 24, 2028 from Bridgetown, Barbados
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Bridgetown, Barbados11 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Port of Kingstown, St. Vincent & the Grenadines · Castries, St. Lucia · Fort-de-France, Martinique · Willis Island · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Roseau, Dominica · Bridgetown, Barbados
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Grenada Private Taxi TourLa Soufrière Volcano Summit HikeCosol Tours +6 more
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from $6,099
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Regent · Seven Seas PrestigeRound-trip
Caribbean 15 nights Feb 16 – Mar 2, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida15 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · St. Georges, Grenada, West Indies · Willis Island · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Oranjestad, Sint Eustatius · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandJost Van DykeBoiling Lake Hike +7 more
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from $11,799
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Regent · Seven Seas PrestigeOne-way
Mediterranean 12 nights Mar 14 – Mar 26, 2028 from Panama City, Panama to Miami, Florida
Panama City, Panama · Kiel Canal, Germany · … · Miami, Florida12 ports
Panama City, Panama · Kiel Canal, Germany · Cartagena, Spain · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Willis Island · St. Georges, Grenada, West Indies · Roseau, Dominica · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Willis Island · Miami, Florida
★ Bucket-list Panama Canal Miraflores LocksPrivate Expert Walking Tour of KielThe Roman Theatre of Cartagena with the Rafael Mon…Zodiac Circumnavigation of Willis Island +6 more
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from $8,599
Book This Cruise@ Cruisebound

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