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
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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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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 Virgin Voyages ×Norwegian ×Visits Samana × Clear all
Showing 13 of 13 sailings
Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 13, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Samana, Dominican Republic · Grand Turk, Turks and Caicos · Cabo Rojo, Dominican Republic · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsHumpback Whale Watching in Samaná BayGibbs Cay Private Stingray Swim & Reef Snorkel
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from $1,966
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Virgin Voyages · Resilient LadyRound-trip
Caribbean Mar 21, 2027 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelHumpback Whale Watching in Samaná BayThe full 27 jumps at the Damajagua Waterfalls
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from $1,005
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Virgin Voyages · Resilient LadyRound-trip
Caribbean Nov 7, 2027 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida6 ports
Miami, Florida · Grand Turk, Turks and Caicos · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelHumpback Whale Watching in Samaná BayThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $1,137
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Virgin Voyages · Resilient LadyRound-trip
Caribbean Nov 20, 2027 from Miami, Florida
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida6 ports
Miami, Florida · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico · Samana, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Maho BeachWalk El Morro & Old San Juan's City WallsHumpback Whale Watching in Samaná Bay +1 more
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from $1,192
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Norwegian · Norwegian DawnRound-trip
Bahamas 10 nights Nov 29 – Dec 9, 2027 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Nassau, Bahamas · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
★ Bucket-list Amelia Island Guided Kayak Tour of Lofton CreekUNEXSOSwim With the Wild Exuma PigsThe full 27 jumps at the Damajagua Waterfalls +3 more
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from $1,089
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Norwegian · Norwegian DawnRound-trip
Caribbean 12 nights Jan 2 – Jan 14, 2028 from Jacksonville, Florida
Jacksonville, Florida · Great Stirrup Cay, Bahamas · … · Jacksonville, Florida10 ports
Jacksonville, Florida · Great Stirrup Cay, Bahamas · Grand Bahama Island · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · San Juan, Puerto Rico · Jacksonville, Florida
★ Bucket-list Amelia Island Guided Kayak Tour of Lofton CreekSilver Cove Private VillaUNEXSOThe full 27 jumps at the Damajagua Waterfalls +5 more
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from $1,108
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Virgin Voyages · Resilient LadyRound-trip
Caribbean Jan 2, 2028 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida6 ports
Miami, Florida · Nassau, Bahamas · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma PigsHumpback Whale Watching in Samaná BayThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $1,065
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Virgin Voyages · Resilient LadyRound-trip
Bahamas Jan 16, 2028 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida6 ports
Miami, Florida · Grand Turk, Turks and Caicos · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelHumpback Whale Watching in Samaná BayThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $1,066
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Norwegian · Norwegian DawnRound-trip
Caribbean 10 nights Jan 18 – Jan 28, 2028 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Puerto Plata, Dominican Republic · Samana, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
★ Bucket-list Amelia Island Guided Kayak Tour of Lofton CreekUNEXSOThe full 27 jumps at the Damajagua WaterfallsHumpback Whale Watching in Samaná Bay +3 more
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from $839
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Norwegian · Norwegian DawnRound-trip
Caribbean 10 nights Jan 28 – Feb 7, 2028 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Great Stirrup Cay, Bahamas · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
★ Bucket-list Amelia Island Guided Kayak Tour of Lofton CreekUNEXSOSilver Cove Private VillaHumpback Whale Watching in Samaná Bay +3 more
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from $1,079
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Norwegian · Norwegian DawnRound-trip
Caribbean 10 nights Feb 7 – Feb 17, 2028 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Great Stirrup Cay, Bahamas · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
★ Bucket-list Amelia Island Guided Kayak Tour of Lofton CreekUNEXSOSilver Cove Private VillaThe full 27 jumps at the Damajagua Waterfalls +3 more
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from $926
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Virgin Voyages · Resilient LadyRound-trip
Bahamas Feb 12, 2028 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida7 ports
Miami, Florida · Grand Turk, Turks and Caicos · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Nassau, Bahamas · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelThe full 27 jumps at the Damajagua WaterfallsHumpback Whale Watching in Samaná Bay +2 more
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from $1,280
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Virgin Voyages · Resilient LadyRound-trip
Bahamas Mar 11, 2028 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida7 ports
Miami, Florida · Grand Turk, Turks and Caicos · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Nassau, Bahamas · Bimini, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelHumpback Whale Watching in Samaná BayThe full 27 jumps at the Damajagua Waterfalls +2 more
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from $1,280
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