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
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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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Filtering Visits Samana ×9–12 nights × Clear all
Showing 7 of 7 sailings
Celebrity · Celebrity SummitRepositioning
Caribbean 9 nights Oct 20 – Oct 29, 2027 from Boston, Massachusetts to San Juan, Puerto Rico
Boston, Massachusetts · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Boston, Massachusetts · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Private Luxury Boston TourThe full 27 jumps at the Damajagua WaterfallsHumpback Whale Watching in Samaná BayPrivate Full-Day Boat Charter +3 more
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from $806
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Royal Caribbean · Serenade of the SeasRound-trip
Caribbean 9 nights Oct 22 – Oct 31, 2027 from Tampa, Florida
Tampa, Florida · Nassau, Bahamas · … · Tampa, Florida6 ports
Tampa, Florida · Nassau, Bahamas · Samana, Dominican Republic · Labadee (Labadie), Haiti · Grand Turk, Turks and Caicos · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterSwim With the Wild Exuma PigsHumpback Whale Watching in Samaná BayGibbs Cay Private Stingray Swim & Reef Snorkel
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from $1,075
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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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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
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
aboard
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