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 Norwegian ×Celebrity ×Visits Samana × Clear all
Showing 9 of 9 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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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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Celebrity · Celebrity BeyondRound-trip
Caribbean 7 nights Dec 26 – Jan 2, 2028 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Bimini, Bahamas · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Bimini, Bahamas · Grand Turk, Turks and Caicos · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowSwim with Wild Dolphins at Honeymoon HarbourGibbs Cay Private Stingray Swim & Reef SnorkelHumpback Whale Watching in Samaná Bay +1 more
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from $1,416
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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
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Celebrity · Celebrity SummitRound-trip
Caribbean Feb 15, 2028 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · San Juan, Puerto Rico · Samana, Dominican Republic · Grand Turk, Turks and Caicos · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowWalk El Morro & Old San Juan's City WallsHumpback Whale Watching in Samaná BayGibbs Cay Private Stingray Swim & Reef Snorkel
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from $566
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Celebrity · Celebrity ApexRound-trip
Bahamas Apr 15, 2028 from Orlando, Florida
Orlando, Florida · Grand Turk, Turks and Caicos · … · Orlando, Florida6 ports
Orlando, Florida · Grand Turk, Turks and Caicos · Samana, Dominican Republic · Perfect Day at CocoCay · Bimini, Bahamas · Orlando, Florida
★ Bucket-list Gibbs Cay Private Stingray Swim & Reef SnorkelHumpback Whale Watching in Samaná BayDaredevil's PeakSwim with Wild Dolphins at Honeymoon Harbour
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from $791
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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