Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

Every cruise here comes with the bucket-list thing at each port and a whole-trip plan — where to fly in, the days before and after, what it all runs. Filter by date, length, line, or the ports it visits.

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Showing 36 of 163 sailings
Celebrity · Celebrity SummitOne-way
Mexico 17 nights Oct 1 – Oct 18, 2026 from Los Angeles, California to Tampa, Florida
Los Angeles, California · Puerto Vallarta, Mexico · … · Tampa, Florida9 ports
Los Angeles, California · Puerto Vallarta, Mexico · Puerto Quetzal, Guatemala · Puntarenas, Costa Rica · Panama Canal, Panama · Cartagena, Colombia · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Warner Bros. Studio Tour HollywoodHidden Beach at Marietas IslandsThe Roman Theatre of Cartagena with the Rafael Mon…Stingray City Sandbar +1 more
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from $1,578
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Carnival · Carnival DreamRound-trip
Caribbean Oct 3, 2026 from Galveston, Texas
Galveston, Texas · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Galveston, Texas
★ Bucket-list Moody GardensStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $632
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Carnival · Carnival MiracleRound-trip
Mexico Oct 12, 2026 from Galveston, Texas
Galveston, Texas · Georgetown, Grand Cayman, Cayman Islands · … · Galveston, Texas7 ports
Galveston, Texas · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Belize City, Belize · Cozumel, Mexico · Galveston, Texas
★ Bucket-list Moody GardensStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Great Blue Hole Flightseeing & Lighthouse Reef Sno… +1 more
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from $843
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Oct 31 – Nov 7, 2026 from Orlando, Florida
Orlando, Florida · Key West, Florida · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Orlando, Florida
★ Bucket-list Dry Tortugas National ParkStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $872
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Disney · Disney MagicRepositioning
Mediterranean 14 nights Nov 6 – Nov 20, 2026 from San Diego, California to Galveston, Texas
San Diego, California · Cabo San Lucas, Mexico · … · Galveston, Texas7 ports
San Diego, California · Cabo San Lucas, Mexico · Puerto Vallarta, Mexico · Panama City, Panama · Cartagena, Spain · Georgetown, Grand Cayman, Cayman Islands · Galveston, Texas
★ Bucket-list San Diego ZooEl Arco & Lover's BeachHidden Beach at Marietas IslandsThe Roman Theatre of Cartagena with the Rafael Mon… +2 more
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from $2,967
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Royal Caribbean · Radiance of the SeasRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2026 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · Costa Maya, Mexico · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelChacchoben Mayan RuinsStingray City Sandbar
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from $522
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Celebrity · Celebrity ApexRound-trip
Mexico 7 nights Nov 14 – Nov 21, 2026 from Orlando, Florida
Orlando, Florida · Nassau, Bahamas · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Orlando, Florida
★ Bucket-list Swim With the Wild Exuma PigsStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $709
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Regent · Seven Seas SplendorOne-way
Mexico 15 nights Nov 15 – Nov 30, 2026 from Miami, Florida to Galveston, Texas
Miami, Florida · Willis Island · … · Galveston, Texas16 ports
Miami, Florida · Willis Island · Willis Island · Willemstad, Curacao · Oranjestad, Sint Eustatius · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Roatan, Honduras · Willis Island · Cozumel, Mexico · Progresso, Mexico · Willis Island · Galveston, Texas
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Full-Day Curaçao Island Tour with Local Ex…The Natural Pool +5 more
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from $9,799
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Carnival · Carnival LegendRound-trip
Caribbean Nov 16, 2026 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $411
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Carnival · Carnival DreamRound-trip
Mexico Nov 21, 2026 from Galveston, Texas
Galveston, Texas · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Galveston, Texas
★ Bucket-list Moody GardensStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $680
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Carnival · Carnival LegendRound-trip
Mexico Nov 21, 2026 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Tampa, Florida6 ports
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Roatan, Honduras · Belize City, Belize · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Great Blue Hole Flightseeing & Lighthouse Reef Sno… +1 more
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from $590
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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Nov 22 – Nov 29, 2026 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · Belize City, Belize · 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…Stingray City Sandbar
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from $580
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Carnival · Carnival MiracleRound-trip
Caribbean Nov 23, 2026 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · … · Galveston, Texas7 ports
Galveston, Texas · Cozumel, Mexico · Belize City, Belize · Roatan, Honduras · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +1 more
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from $630
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 2026 from Orlando, Florida
Orlando, Florida · Key West, Florida · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Orlando, Florida
★ Bucket-list Dry Tortugas National ParkStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $1,025
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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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Carnival · Carnival LegendRound-trip
Caribbean Nov 29, 2026 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelStingray City Sandbar
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from $581
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Regent · Seven Seas SplendorRound-trip
Mexico 11 nights Nov 30 – Dec 11, 2026 from Galveston, Texas
Galveston, Texas · Willis Island · … · Galveston, Texas12 ports
Galveston, Texas · Willis Island · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Roatan, Honduras · Belize City, Belize · Costa Maya, Mexico · Cozumel, Mexico · Willis Island · Willis Island · Galveston, Texas
★ Bucket-list Moody GardensZodiac Circumnavigation of Willis IslandStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +3 more
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from $7,799
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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, Florida11 ports
Miami, Florida · Willis Island · 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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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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Regent · Seven Seas SplendorRound-trip
Caribbean 17 nights Dec 11 – Dec 28, 2026 from Galveston, Texas
Galveston, Texas · Willis Island · … · Galveston, Texas18 ports
Galveston, Texas · Willis Island · Willis Island · Montego Bay, Jamaica · Ocho Rios, Jamaica · Willis Island · Punta Cana, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Gustavia, St. Barts · St. John's, Antigua · Willis Island · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Willis Island · Willis Island · Galveston, Texas
★ Bucket-list Moody GardensZodiac Circumnavigation of Willis IslandWalk El Morro & Old San Juan's City WallsJost Van Dyke +3 more
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from $10,299
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Celebrity · Celebrity ApexRound-trip
Mexico 7 nights Dec 12 – Dec 19, 2026 from Orlando, Florida
Orlando, Florida · Key West, Florida · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Orlando, Florida
★ Bucket-list Dry Tortugas National ParkStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $943
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Cunard · Queen ElizabethRepositioning
Mexico 33 nights Dec 17 – Jan 19, 2027 from Miami, Florida to Southampton, England
Miami, Florida · San Juan, Puerto Rico · … · Southampton, England17 ports
Miami, Florida · San Juan, Puerto Rico · Antigua, Antigua & Barbuda · St. Lucia, Caribbean · Bridgetown, Barbados · Bridgetown, Barbados · Philipsburg, St. Maarten · Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Miami, Florida · Praia da Vitoria, Portugal · Ponta Delgada, Azores, Portugal · Southampton, England
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsSwim with wild green sea turtles + two shipwrecks…Random Wind 'Paradise Day Sail' +5 more
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from $5,999
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Carnival · Carnival DreamRound-trip
Mexico Dec 19, 2026 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Georgetown, Grand Cayman, Cayman Islands · Montego Bay, Jamaica · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelStingray City Sandbar
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from $1,034
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Carnival · Carnival LegendRound-trip
Caribbean Dec 19, 2026 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Tampa, Florida6 ports
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Roatan, Honduras · Belize City, Belize · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Great Blue Hole Flightseeing & Lighthouse Reef Sno… +1 more
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from $886
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Royal Caribbean · Jewel of the SeasRound-trip
Mexico 8 nights Dec 20 – Dec 28, 2026 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · … · Tampa, Florida6 ports
Tampa, Florida · Cozumel, Mexico · Belize City, Belize · Costa Maya, Mexico · 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 +1 more
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from $772
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Carnival · Carnival ParadiseRound-trip
Mexico Dec 21, 2026 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $714
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Regent · Seven Seas MarinerOne-way
Caribbean 14 nights Dec 21 – Jan 4, 2027 from Tampa, Florida to Miami, Florida
Tampa, Florida · Willis Island · … · Miami, Florida15 ports
Tampa, Florida · Willis Island · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Willis Island · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Willis Island · Willis Island · Miami, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterZodiac Circumnavigation of Willis IslandStingray City SandbarThe Natural Pool +6 more
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from $9,899
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Celebrity · Celebrity ApexRound-trip
Caribbean Dec 26, 2026 from Orlando, Florida
Orlando, Florida · Key West, Florida · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Orlando, Florida
★ Bucket-list Dry Tortugas National ParkStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $1,559
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Carnival · Carnival LegendRound-trip
Caribbean Dec 27, 2026 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelStingray City Sandbar
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from $1,044
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Royal Caribbean · Radiance of the SeasRound-trip
Caribbean 7 nights Jan 2 – Jan 9, 2027 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · Costa Maya, Mexico · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelChacchoben Mayan RuinsStingray City Sandbar
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from $558
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Carnival · Carnival LegendRound-trip
Mexico Jan 3, 2027 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $500
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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
Book This Cruise@ Cruisebound
Carnival · Carnival MiracleRound-trip
Mexico Jan 4, 2027 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · … · Galveston, Texas7 ports
Galveston, Texas · Cozumel, Mexico · Belize City, Belize · Roatan, Honduras · Montego Bay, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha… +1 more
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from $573
Book This Cruise@ Cruisebound
Carnival · Carnival ParadiseRound-trip
Caribbean Jan 4, 2027 from Tampa, Florida
Tampa, Florida · Georgetown, Grand Cayman, Cayman Islands · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterStingray City SandbarEl Cielo + Palancar + Columbia 3-Stop Snorkel
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from $251
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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
Book This Cruise@ Cruisebound
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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