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
My result then click any cruise row to open it
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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+ pick specific cruise lines · 2 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 Regent ×Cunard ×Visits Montego Bay × Clear all
Showing 12 of 12 sailings
Cunard · Queen ElizabethRound-trip
Caribbean 21 nights Nov 5 – Nov 26, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida14 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsAdventure AntiguaGros Piton Summit Hike +8 more
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from $1,945
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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 +6 more
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from $9,799
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Cunard · Queen ElizabethRound-trip
Mexico 9 nights Nov 17 – Nov 26, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida7 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarMartha Brae River Bamboo RaftingHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +2 more
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from $849
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Cunard · Queen ElizabethRound-trip
Caribbean 21 nights Nov 26 – Dec 17, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida14 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsAdventure AntiguaGros Piton Summit Hike +8 more
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from $1,680
Book This Cruise@ Cruisebound
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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Cunard · Queen ElizabethRound-trip
Mexico 9 nights Dec 8 – Dec 17, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida7 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarMartha Brae River Bamboo RaftingHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +2 more
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from $849
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Regent · Seven Seas GrandeurRound-trip
Mexico 10 nights Dec 9 – Dec 19, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida11 ports
Miami, Florida · Willis Island · Costa Maya, Mexico · Belize City, Belize · Harvest Caye, Belize · Roatan, Honduras · Willis Island · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandChacchoben Mayan RuinsGreat Blue Hole Flightseeing & Lighthouse Reef Sno… +4 more
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from $6,849
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Regent · Seven Seas MarinerRound-trip
Caribbean 10 nights Dec 11 – Dec 21, 2026 from Tampa, Florida
Tampa, Florida · Willis Island · … · Tampa, Florida11 ports
Tampa, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Willis Island · Roatan, Honduras · Belize City, Belize · Costa Maya, Mexico · Cozumel, Mexico · Willis Island · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterZodiac Circumnavigation of Willis IslandStingray City SandbarMartha Brae River Bamboo Rafting +4 more
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from $7,499
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Regent · Seven Seas SplendorRound-trip
Caribbean 17 nights Dec 11 – Dec 28, 2026 from Galveston, Texas
Galveston, Texas · Willis Island · … · Galveston, Texas15 ports
Galveston, Texas · Willis Island · Montego Bay, Jamaica · Ocho Rios, Jamaica · Willis Island · Punta Cana, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Gustavia, St. Barts · St. John's, Antigua · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Galveston, Texas
★ Bucket-list Moody GardensZodiac Circumnavigation of Willis IslandMartha Brae River Bamboo RaftingBlue Hole +5 more
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from $10,299
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Cunard · Queen ElizabethRepositioning
Mexico 33 nights Dec 17 – Jan 19, 2027 from Miami, Florida to Southampton, England
Miami, Florida · San Juan, Puerto Rico · … · Southampton, England16 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Philipsburg, St. Maarten · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida · Praia da Vitoria, Portugal · Ponta Delgada, Azores, Portugal · Southampton, England
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsAdventure AntiguaGros Piton Summit Hike +10 more
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from $5,999
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Regent · Seven Seas SplendorOne-way
Caribbean 14 nights Dec 28 – Jan 11, 2027 from Galveston, Texas to Miami, Florida
Galveston, Texas · Willis Island · … · Miami, Florida14 ports
Galveston, Texas · Willis Island · Cozumel, Mexico · Belize City, Belize · Santo Tomas de Castilla, Guatemala · Roatan, Honduras · Willis Island · Montego Bay, Jamaica · Willis Island · Willemstad, Curacao · Oranjestad, Sint Eustatius · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Miami, Florida
★ Bucket-list Moody GardensZodiac Circumnavigation of Willis IslandEl Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno… +7 more
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from $9,899
Book This Cruise@ Cruisebound
Cunard · Queen ElizabethRound-trip
Caribbean 9 nights Dec 29 – Jan 7, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida7 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarMartha Brae River Bamboo RaftingHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +2 more
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from $1,299
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.

19 lines
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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