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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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 Tampa ×9–12 nights × Clear all
Showing 14 of 14 sailings
Norwegian · Norwegian GemRound-trip
Caribbean 12 nights Nov 28 – Dec 10, 2026 from Tampa, Florida
Tampa, Florida · San Juan, Puerto Rico · … · Tampa, Florida9 ports
Tampa, Florida · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterWalk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater Hike +4 more
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from $941
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Regent · Seven Seas MarinerOne-way
Caribbean 10 nights Dec 1 – Dec 11, 2026 from Miami, Florida to Tampa, Florida
Miami, Florida · Willis Island · … · Tampa, Florida10 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Tampa, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +3 more
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from $7,900
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Royal Caribbean · Jewel of the SeasRound-trip
Caribbean 9 nights Dec 7 – Dec 16, 2026 from Tampa, Florida
Tampa, Florida · San Juan, Puerto Rico · … · Tampa, Florida6 ports
Tampa, Florida · San Juan, Puerto Rico · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Full-Day Boat Charter +1 more
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from $708
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Norwegian · Norwegian GemRound-trip
Bahamas 11 nights Dec 10 – Dec 21, 2026 from Tampa, Florida
Tampa, Florida · Great Stirrup Cay, Bahamas · … · Tampa, Florida8 ports
Tampa, Florida · Great Stirrup Cay, Bahamas · Cabo Rojo, Dominican Republic · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterSilver Cove Private VillaArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +2 more
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from $834
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Regent · Seven Seas MarinerRound-trip
Caribbean 10 nights Dec 11 – Dec 21, 2026 from Tampa, Florida
Tampa, Florida · Willis Island · … · Tampa, Florida11 ports
Tampa, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Willis Island · Roatan, Honduras · Belize City, Belize · Costa Maya, Mexico · Cozumel, Mexico · Willis Island · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterZodiac Circumnavigation of Willis IslandStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +3 more
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from $7,499
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Celebrity · Celebrity SummitRound-trip
Mexico 9 nights Jan 3 – Jan 12, 2027 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Tampa, Florida7 ports
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Chacchoben Mayan Ruins +1 more
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from $699
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Norwegian · Norwegian GemRound-trip
Caribbean 10 nights Jan 4 – Jan 14, 2027 from Tampa, Florida
Tampa, Florida · Cabo Rojo, Dominican Republic · … · Tampa, Florida7 ports
Tampa, Florida · Cabo Rojo, Dominican Republic · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Blue Hole & Secret Falls +1 more
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from $780
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Norwegian · Norwegian GemRound-trip
Caribbean 10 nights Jan 18 – Jan 28, 2027 from Tampa, Florida
Tampa, Florida · Cabo Rojo, Dominican Republic · … · Tampa, Florida7 ports
Tampa, Florida · Cabo Rojo, Dominican Republic · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterPrivate Full-Day Curaçao Island Tour with Local Ex…ArubaBlue Hole & Secret Falls +1 more
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from $968
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Norwegian · Norwegian GemRound-trip
Bahamas 9 nights Feb 12 – Feb 21, 2027 from Tampa, Florida
Tampa, Florida · Key West, Florida · … · Tampa, Florida7 ports
Tampa, Florida · Key West, Florida · Great Stirrup Cay, Bahamas · Cabo Rojo, Dominican Republic · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterDry Tortugas National ParkSilver Cove Private VillaBlue Hole & Secret Falls +1 more
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from $972
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Celebrity · Celebrity SummitRound-trip
Mexico 10 nights Feb 14 – Feb 24, 2027 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · … · Tampa, Florida8 ports
Tampa, Florida · Cozumel, Mexico · Belize City, Belize · Costa Maya, Mexico · Roatan, Honduras · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno…Chacchoben Mayan Ruins +3 more
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from $837
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Norwegian · Norwegian GemRound-trip
Bahamas 11 nights Feb 21 – Mar 4, 2027 from Tampa, Florida
Tampa, Florida · Great Stirrup Cay, Bahamas · … · Tampa, Florida8 ports
Tampa, Florida · Great Stirrup Cay, Bahamas · Cabo Rojo, Dominican Republic · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterSilver Cove Private VillaArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +2 more
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from $1,167
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Norwegian · Norwegian GemOne-way
Caribbean 10 nights Apr 3 – Apr 13, 2027 from Tampa, Florida to New York, New York
Tampa, Florida · Cabo Rojo, Dominican Republic · … · New York, New York6 ports
Tampa, Florida · Cabo Rojo, Dominican Republic · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Puerto Plata, Dominican Republic · New York, New York
★ Bucket-list Clearwater Beach Private Luxury CharterPrivate Full-Day Curaçao Island Tour with Local Ex…ArubaThe full 27 jumps at the Damajagua Waterfalls +1 more
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from $999
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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 PigsGibbs Cay Private Stingray Swim & Reef Snorkel
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from $1,075
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Azamara · Azamara QuestRound-trip
Caribbean 11 nights Mar 22 – Apr 2, 2028 from Miami, Florida
Miami, Florida · Key West, Florida · … · Miami, Florida7 ports
Miami, Florida · Key West, Florida · Tampa, Florida · Mobile, Alabama · New Orleans, Louisiana · Cozumel, Mexico · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Dry Tortugas National ParkClearwater Beach Private Luxury CharterSteamboat Natchez +1 more
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from $3,521
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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