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.

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Filtering Virgin Voyages ×Visits Georgetown × Clear all
Showing 40 of 40 sailings
Virgin Voyages · Resilient LadyRound-trip
Bahamas Jun 13, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,099
Book This Cruise@ Cruisebound
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 SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,210
Book This Cruise@ Cruisebound
Virgin Voyages · Scarlet LadyRound-trip
Caribbean Nov 9, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,255
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…Stingray 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 SandbarSwim 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 SandbarSwim 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…Stingray 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 SandbarSwim With the Wild Exuma PigsSwim with Wild Dolphins at Honeymoon Harbour
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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…Stingray 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 SandbarSwim With the Wild Exuma PigsSwim with Wild Dolphins at Honeymoon Harbour
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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 HarbourStingray City Sandbar
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from $1,006
Book This Cruise@ Cruisebound
Virgin Voyages · Scarlet LadyRound-trip
Caribbean Mar 29, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,097
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 ParkStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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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 SandbarSwim With the Wild Exuma PigsSwim with Wild Dolphins at Honeymoon Harbour
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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 SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $2,018
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Caribbean Apr 23, 2027 from Miami, Florida
Miami, Florida · Bimini, Bahamas · Georgetown, Grand Cayman, Cayman Islands · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim with Wild Dolphins at Honeymoon HarbourStingray City Sandbar
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from $1,055
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas May 10, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $999
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean May 24, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
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from $1,049
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Jun 7, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,051
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Jul 5, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,051
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Jul 19, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,051
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Aug 30, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,001
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Sep 18, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $952
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Sep 27, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $951
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Nov 22, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $850
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…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,007
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 6, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $800
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 SandbarSwim With the Wild Exuma PigsSwim with Wild Dolphins at Honeymoon Harbour
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 SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
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 PigsStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $2,165
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Jan 3, 2028 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $800
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 ParkStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,093
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 17, 2028 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $800
Book This Cruise@ Cruisebound
Virgin Voyages · Resilient LadyRound-trip
Bahamas Jan 23, 2028 from Miami, Florida
Miami, Florida · Key West, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkStingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $950
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…Stingray 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…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $1,006
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Feb 28, 2028 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $850
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Bahamas Mar 13, 2028 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarSwim with Wild Dolphins at Honeymoon Harbour
View →
from $900
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…Stingray 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…Stingray 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.

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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