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
Cruise level tap one or more Luxury Premium Contemporary River
+ 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 AmaWaterways ×Virgin Voyages ×Visits Ocho Rios × Clear all
Showing 22 of 22 sailings
Virgin Voyages · Resilient LadyRound-trip
Bahamas Nov 1, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim with Wild Dolphins at Honeymoon Harbour
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from $1,210
Book This Cruise@ Cruisebound
Virgin Voyages · Scarlet LadyRound-trip
Bahamas Nov 23, 2026 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleSwim with Wild Dolphins at Honeymoon Harbour
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from $1,223
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Nov 29, 2026 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,066
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Dec 13, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim with Wild Dolphins at Honeymoon Harbour
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from $1,126
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Dec 27, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim with Wild Dolphins at Honeymoon Harbour
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from $1,975
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Bahamas Jan 10, 2027 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,066
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Feb 7, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida6 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Nassau, Bahamas · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim With the Wild Exuma Pigs +1 more
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from $1,219
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Feb 21, 2027 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,415
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Feb 28, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida6 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Nassau, Bahamas · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim With the Wild Exuma Pigs +1 more
View →
from $1,219
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Mar 7, 2027 from Miami, Florida
Miami, Florida · Bimini, Bahamas · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim with Wild Dolphins at Honeymoon HarbourBlue HoleStingray City Sandbar
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from $1,006
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Apr 4, 2027 from Miami, Florida
Miami, Florida · Key West, Florida · … · Miami, Florida6 ports
Miami, Florida · Key West, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkBlue HoleStingray City Sandbar +1 more
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from $1,307
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Apr 11, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida6 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Nassau, Bahamas · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim With the Wild Exuma Pigs +1 more
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from $1,289
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Apr 15, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim with Wild Dolphins at Honeymoon Harbour
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from $2,018
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Bahamas Nov 28, 2027 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,007
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Bahamas Dec 12, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida6 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Nassau, Bahamas · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim With the Wild Exuma Pigs +1 more
View →
from $1,080
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 20, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleSwim with Wild Dolphins at Honeymoon Harbour
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from $1,342
Book This Cruise@ Cruisebound
Virgin Voyages · Brilliant LadyRound-trip
Bahamas Dec 28, 2027 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida6 ports
Miami, Florida · Nassau, Bahamas · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma PigsBlue HoleStingray City Sandbar +1 more
View →
from $2,165
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Jan 9, 2028 from Miami, Florida
Miami, Florida · Key West, Florida · … · Miami, Florida6 ports
Miami, Florida · Key West, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkBlue HoleStingray City Sandbar +1 more
View →
from $1,093
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Feb 6, 2028 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,006
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Feb 20, 2028 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,006
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Mar 19, 2028 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,006
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Bahamas Apr 2, 2028 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,066
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