Bucket-List Cruise Adventures

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Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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Filtering Caribbean ×Celebrity ×Round trip × Clear all
Showing 36 of 122 sailings
Celebrity · Celebrity SummitRound-trip
Bahamas 7 nights Oct 18 – Oct 25, 2026 from Tampa, Florida
Tampa, Florida · Key West, Florida · Bimini, Bahamas · Nassau, Bahamas · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterDry Tortugas National ParkSwim with Wild Dolphins at Honeymoon HarbourSwim With the Wild Exuma Pigs
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from $647
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Celebrity · Celebrity SummitRound-trip
Mexico 7 nights Oct 25 – Nov 1, 2026 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · Belize City, Belize · Costa Maya, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno…Chacchoben Mayan Ruins
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from $670
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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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Celebrity · Celebrity SummitRound-trip
Bahamas 7 nights Nov 1 – Nov 8, 2026 from Tampa, Florida
Tampa, Florida · Key West, Florida · Bimini, Bahamas · Nassau, Bahamas · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterDry Tortugas National ParkSwim with Wild Dolphins at Honeymoon HarbourSwim With the Wild Exuma Pigs
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from $707
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $938
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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Nov 8 – Nov 15, 2026 from Tampa, Florida
Tampa, Florida · Belize City, Belize · Cozumel, Mexico · Costa Maya, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterGreat Blue Hole Flightseeing & Lighthouse Reef Sno…El Cielo + Palancar + Columbia 3-Stop SnorkelChacchoben Mayan Ruins
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from $1,124
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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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Celebrity · Celebrity SummitRound-trip
Bahamas 7 nights Nov 15 – Nov 22, 2026 from Tampa, Florida
Tampa, Florida · Key West, Florida · Bimini, Bahamas · Nassau, Bahamas · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterDry Tortugas National ParkSwim with Wild Dolphins at Honeymoon HarbourSwim With the Wild Exuma Pigs
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from $772
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 11 nights Nov 17 – Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Fort-de-France, Martinique · Roseau, Dominica · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykePrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +4 more
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from $917
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,788
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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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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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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $910
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Celebrity · Celebrity SummitRound-trip
Bahamas 7 nights Nov 29 – Dec 6, 2026 from Tampa, Florida
Tampa, Florida · Key West, Florida · Bimini, Bahamas · Nassau, Bahamas · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterDry Tortugas National ParkSwim with Wild Dolphins at Honeymoon HarbourSwim With the Wild Exuma Pigs
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from $586
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
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from $1,517
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Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
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from $603
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Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from Tampa, Florida
Tampa, Florida · Cozumel, Mexico · Belize City, Belize · Costa Maya, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterEl Cielo + Palancar + Columbia 3-Stop SnorkelGreat Blue Hole Flightseeing & Lighthouse Reef Sno…Chacchoben Mayan Ruins
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from $612
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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
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
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from $582
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRound-trip
Bahamas 7 nights Dec 13 – Dec 20, 2026 from Tampa, Florida
Tampa, Florida · Bimini, Bahamas · Key West, Florida · Grand Bahama Island · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterSwim with Wild Dolphins at Honeymoon HarbourDry Tortugas National ParkUNEXSO
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from $570
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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Dec 19 – Dec 26, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $1,285
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 19 – Dec 26, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsJost Van DykeMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
View →
from $656
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRound-trip
Mexico 7 nights Dec 20 – Dec 27, 2026 from Tampa, Florida
Tampa, Florida · Nassau, Bahamas · Bimini, Bahamas · Cozumel, Mexico · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterSwim With the Wild Exuma PigsSwim with Wild Dolphins at Honeymoon HarbourEl Cielo + Palancar + Columbia 3-Stop Snorkel
View →
from $754
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 26 – Jan 2, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $817
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitRound-trip
Bahamas Dec 27, 2026 from Tampa, Florida
Tampa, Florida · Key West, Florida · Bimini, Bahamas · Nassau, Bahamas · Tampa, Florida
★ Bucket-list Clearwater Beach Private Luxury CharterDry Tortugas National ParkSwim with Wild Dolphins at Honeymoon HarbourSwim With the Wild Exuma Pigs
View →
from $792
Book This Cruise@ Cruisebound
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 2 – Jan 9, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $615
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 2 – Jan 9, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
View →
from $645
Book This Cruise@ Cruisebound
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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Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 9 – Jan 16, 2027 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
View →
from $702
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 9 – Jan 16, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $517
Book This Cruise@ Cruisebound
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 16 – Jan 23, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $907
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 16 – Jan 23, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater HikeBoiling Lake Hike +2 more
View →
from $733
Book This Cruise@ Cruisebound
Celebrity · Celebrity ApexRound-trip
Mexico 7 nights Jan 23 – Jan 30, 2027 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
View →
from $688
Book This Cruise@ Cruisebound
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 23 – Jan 30, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $501
Book This Cruise@ Cruisebound
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 30 – Feb 6, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike
View →
from $982
Book This Cruise@ Cruisebound
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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