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.

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Showing 36 of 540 sailings
Princess · Caribbean PrincessRound-trip
Bahamas 14 nights Jun 28 – Jul 12, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Nassau, Bahamas · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · Nassau, Bahamas · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexSwim With the Wild Exuma PigsPrivate Bungalow Day27 Charcos of Damajagua +2 more
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from $1,721
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Royal Caribbean · Independence of the SeasRound-trip
Bermuda 9 nights Jul 2 – Jul 11, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Island Wrap-Around Van Tour of BermudaRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $1,677
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MSC Cruises · MSC World AmericaRound-trip
Caribbean 14 nights Jul 4 – Jul 18, 2026 from Miami, Florida
Miami, Florida · Roatan, Honduras · … · Miami, Florida10 ports
Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Chacchoben Mayan RuinsEl Cielo + Palancar + Columbia 3-Stop Snorkel +3 more
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from $1,576
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MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Jul 25 – Aug 8, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,565
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Princess · Caribbean PrincessRound-trip
Caribbean 14 nights Jul 26 – Aug 9, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Grand Turk, Turks and Caicos · … · Port Canaveral, Florida9 ports
Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexGibbs Cay Private Stingray Swim & Reef Snorkel27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls
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from $976
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Royal Caribbean · Independence of the SeasRound-trip
Caribbean 9 nights Jul 30 – Aug 8, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · … · Cape Liberty (Bayonne), New Jersey6 ports
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Island Wrap-Around Van Tour of BermudaRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
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from $1,300
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MSC Cruises · MSC World AmericaRound-trip
Caribbean 14 nights Aug 8 – Aug 22, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,610
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Princess · Caribbean PrincessRound-trip
Caribbean 14 nights Aug 16 – Aug 30, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Grand Turk, Turks and Caicos · … · Port Canaveral, Florida9 ports
Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexGibbs Cay Private Stingray Swim & Reef Snorkel27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls
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from $1,136
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Norwegian · Norwegian EscapeRound-trip
Caribbean 10 nights Aug 19 – Aug 29, 2026 from New York, New York
New York, New York · San Juan, Puerto Rico · … · New York, New York7 ports
New York, New York · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Puerto Plata, Dominican Republic · New York, New York
★ Bucket-list Manhattan Helicopter TourWalk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Private Catamaran Sail & Snorkel at Honeymoon Beac… +2 more
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from $1,264
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MSC Cruises · MSC World AmericaRound-trip
Caribbean 14 nights Aug 22 – Sep 5, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,351
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Princess · Caribbean PrincessRound-trip
Bahamas 14 nights Aug 23 – Sep 6, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Grand Turk, Turks and Caicos · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida · Nassau, Bahamas · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexGibbs Cay Private Stingray Swim & Reef Snorkel27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls +2 more
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from $913
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MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Aug 29 – Sep 12, 2026 from Miami, Florida
Miami, Florida · Roatan, Honduras · … · Miami, Florida10 ports
Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Chacchoben Mayan RuinsEl Cielo + Palancar + Columbia 3-Stop Snorkel +3 more
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from $1,762
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Princess · Caribbean PrincessRound-trip
Bahamas 14 nights Aug 30 – Sep 13, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Nassau, Bahamas · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · Nassau, Bahamas · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexSwim With the Wild Exuma PigsPrivate Bungalow Day27 Charcos of Damajagua +2 more
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from $870
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MSC Cruises · MSC World AmericaRound-trip
Caribbean 14 nights Sep 5 – Sep 19, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,273
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Princess · Caribbean PrincessRound-trip
Caribbean 14 nights Sep 6 – Sep 20, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Grand Turk, Turks and Caicos · … · Port Canaveral, Florida9 ports
Port Canaveral, Florida · Grand Turk, Turks and Caicos · Amber Cove, Dominican Republic · San Juan, Puerto Rico · Port Canaveral, Florida · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexGibbs Cay Private Stingray Swim & Reef Snorkel27 Charcos of DamajaguaWalk El Morro & Old San Juan's City Walls
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from $1,210
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Royal Caribbean · Freedom of the SeasRound-trip
Bahamas 9 nights Sep 10 – Sep 19, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · … · Miami, Florida6 ports
Miami, Florida · Perfect Day at CocoCay · Cabo Rojo, Dominican Republic · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Daredevil's PeakPrivate Full-Day Curaçao Island Tour with Local Ex…Aruba
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from $841
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Princess · Regal PrincessRound-trip
Caribbean 14 nights Sep 19 – Oct 3, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Roatan, Honduras · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Roatan, Honduras · Belize City, Belize · Cozumel, Mexico · Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Great Blue Hole Flightseeing & Lighthouse Reef Sno…El Cielo + Palancar + Columbia 3-Stop Snorkel +3 more
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from $940
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Princess · Caribbean PrincessRound-trip
Bahamas 14 nights Sep 20 – Oct 4, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Nassau, Bahamas · … · Port Canaveral, Florida11 ports
Port Canaveral, Florida · Nassau, Bahamas · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida · Nassau, Bahamas · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexSwim With the Wild Exuma PigsPrivate Bungalow Day27 Charcos of Damajagua +1 more
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from $924
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Royal Caribbean · Freedom of the SeasRound-trip
Bahamas 9 nights Sep 24 – Oct 3, 2026 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida6 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Cabo Rojo, Dominican Republic · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Swim With the Wild Exuma Pigs
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from $765
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Princess · Regal PrincessRound-trip
Caribbean 14 nights Sep 26 – Oct 10, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Amber Cove, Dominican Republic · San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort Lauderdale (Port Everglades), Florida · Roatan, Honduras · Belize City, Belize · Cozumel, Mexico · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show27 Charcos of DamajaguaWalk El Morro & Old San Juan's City WallsMaho Beach +3 more
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from $922
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MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Oct 3 – Oct 17, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,400
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Princess · Regal PrincessRound-trip
Bahamas 14 nights Oct 3 – Oct 17, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Roatan, Honduras · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · Roatan, Honduras · Belize City, Belize · Cozumel, Mexico · Fort Lauderdale (Port Everglades), Florida · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowHold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Great Blue Hole Flightseeing & Lighthouse Reef Sno…El Cielo + Palancar + Columbia 3-Stop Snorkel +4 more
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from $1,082
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Princess · Caribbean PrincessRound-trip
Bahamas 14 nights Oct 4 – Oct 18, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · San Juan, Puerto Rico · … · Port Canaveral, Florida10 ports
Port Canaveral, Florida · San Juan, Puerto Rico · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida · Nassau, Bahamas · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Port Canaveral, Florida
★ Bucket-list Kennedy Space Center Visitor ComplexWalk El Morro & Old San Juan's City Walls27 Charcos of DamajaguaGibbs Cay Private Stingray Swim & Reef Snorkel +2 more
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from $848
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Royal Caribbean · Freedom of the SeasRound-trip
Caribbean 9 nights Oct 8 – Oct 17, 2026 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida6 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Cabo Rojo, Dominican Republic · Perfect Day at CocoCay · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Daredevil's Peak
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from $552
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MSC Cruises · MSC World AmericaRound-trip
Bahamas 14 nights Oct 10 – Oct 24, 2026 from Miami, Florida
Miami, Florida · Roatan, Honduras · … · Miami, Florida10 ports
Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Hold a Sloth at Daniel Johnson's Monkey & Sloth Ha…Chacchoben Mayan RuinsEl Cielo + Palancar + Columbia 3-Stop Snorkel +3 more
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from $1,260
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Norwegian · Norwegian VivaRepositioning
Caribbean 17 nights Oct 14 – Oct 31, 2026 from Barcelona, Spain to Galveston, Texas
Barcelona, Spain · Alicante, Spain · … · Galveston, Texas9 ports
Barcelona, Spain · Alicante, Spain · Motril, Spain · Funchal, Madeira, Portugal · Philipsburg, St. Maarten · La Romana, Dominican Republic · Cabo Rojo, Dominican Republic · Falmouth, Jamaica · Galveston, Texas
★ Bucket-list Sagrada FamiliaCastillo de Santa BárbaraPico do Arieiro to Pico RuivoRandom Wind 'Paradise Day Sail' +3 more
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from $1,149
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Princess · Coral PrincessRound-trip
Caribbean 14 nights Oct 15 – Oct 29, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · … · Fort Lauderdale (Port Everglades), Florida10 ports
Fort Lauderdale (Port Everglades), Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Martinique · Dominica, Caribbean · St. Georges, Grenada, West Indies · Port of Spain, Trinidad · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowMaho BeachMt. Liamuiga Volcano Crater HikeBoiling Lake & Valley of Desolation +3 more
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from $1,489
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MSC Cruises · MSC PoesiaRound-trip
Caribbean 15 nights Oct 17 – Nov 1, 2026 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida10 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Ocho Rios, Jamaica · Miami, Florida · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Cabo Rojo, Dominican Republic · Ocho Rios, Jamaica · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue HoleKlein Bonaire +2 more
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from $1,169
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MSC Cruises · MSC World AmericaRound-trip
Mexico 14 nights Oct 17 – Oct 31, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Ocean Cay, Bahamas · Miami, Florida · Roatan, Honduras · Costa Maya, Mexico · Cozumel, Mexico · Ocean Cay, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsShipwreck Snorkel Safari +3 more
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from $1,192
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Princess · Regal PrincessRound-trip
Mexico 14 nights Oct 17 – Oct 31, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Princess Cays, Bahamas · … · Fort Lauderdale (Port Everglades), Florida9 ports
Fort Lauderdale (Port Everglades), Florida · Princess Cays, Bahamas · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Fort Lauderdale (Port Everglades), Florida · Cozumel, Mexico · Belize City, Belize · Roatan, Honduras · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Bungalow Day27 Charcos of DamajaguaGibbs Cay Private Stingray Swim & Reef Snorkel +3 more
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from $878
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Holland America · Nieuw AmsterdamRound-trip
Bahamas 21 nights Oct 18 – Nov 8, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · … · Fort Lauderdale (Port Everglades), Florida15 ports
Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · Port of Oranjestad, Aruba, Caribbean · Cartagena, Colombia · Gatun Lake, Panama Canal, Panama · Panama Canal, Panama · Colon, Panama · Puerto Limon, Costa Rica · Georgetown, Grand Cayman, Cayman Islands · Fort Lauderdale (Port Everglades), Florida · Cabo Rojo, Dominican Republic · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Half Moon Cay (Little San Salvador Island), Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowHorseback Riding by Land & SeaArubaThe Roman Theatre of Cartagena with the Rafael Mon… +3 more
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from $1,934
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Princess · Caribbean PrincessOne-way
Caribbean 12 nights Oct 18 – Oct 30, 2026 from Port Canaveral, Florida to Fort Lauderdale (Port Everglades), Florida
Port Canaveral, Florida · Port of Oranjestad, Aruba, Caribbean · … · Fort Lauderdale (Port Everglades), Florida8 ports
Port Canaveral, Florida · Port of Oranjestad, Aruba, Caribbean · Curacao, Caribbean · Kralendijk, Bonaire, Dutch Antilles · Amber Cove, Dominican Republic · Grand Turk, Turks and Caicos · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Kennedy Space Center Visitor ComplexArubaKlein Curaçao Private Day TripKlein Bonaire +4 more
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from $824
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MSC Cruises · MSC PoesiaRound-trip
Caribbean 10 nights Oct 22 – Nov 1, 2026 from Miami, Florida
Miami, Florida · Kralendijk, Bonaire, Dutch Antilles · … · Miami, Florida7 ports
Miami, Florida · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Cabo Rojo, Dominican Republic · Ocho Rios, Jamaica · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Klein BonaireArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +1 more
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from $818
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Royal Caribbean · Freedom of the SeasRound-trip
Bahamas 9 nights Oct 22 – Oct 31, 2026 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida6 ports
Miami, Florida · Nassau, Bahamas · Cabo Rojo, Dominican Republic · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Swim With the Wild Exuma PigsPrivate Full-Day Curaçao Island Tour with Local Ex…Aruba
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from $782
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Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Oct 22 – Nov 1, 2026 from Baltimore, Maryland to San Juan, Puerto Rico
Baltimore, Maryland · Grand Turk, Turks and Caicos · … · San Juan, Puerto Rico8 ports
Baltimore, Maryland · Grand Turk, Turks and Caicos · Philipsburg, St. Maarten · Roseau, Dominica · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Gibbs Cay Private Stingray Swim & Reef SnorkelRandom Wind 'Paradise Day Sail'Boiling Lake HikeMount Pelée & Saint-Pierre +3 more
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from $916
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Norwegian · Norwegian SunOne-way
Bermuda 13 nights Oct 24 – Nov 6, 2026 from New York, New York to Miami, Florida
New York, New York · Royal Naval Dockyard, Bermuda · … · Miami, Florida10 ports
New York, New York · Royal Naval Dockyard, Bermuda · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cabo Rojo, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +5 more
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from $1,257
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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