Tropical Caribbean Cruises

Tropical Caribbean cruises to Key West are ideal as a family cruise or a romantic adventure. Home to several literary legends, including Ernest Hemingway and Judy Blume, Key West has plenty of character, and plenty of characters. Swaying palm trees and shimmering waters are ubiquitous in these parts, but only tropical cruises to Key West deliver sunset parties at Mallory Square and live music on Duval Street, plus scurrying chickens, gentle manatees and the southern most point in the continental U.S.A. Take a Fort Lauderdale to Key West cruise to experience this tropical cruise vacation destination or check out our other ports and Caribbean itineraries.

Great to be Back!

2021 Caribbean Cruises Begin Sailing October 23rd

Island hop the Caribbean on cruises from Fort Lauderdale. Our featured itineraries depart Florida to Key West, Half Moon Cay and Jamaica.

Holland America Line cruises from Fort Lauderdale to the Caribbean are available for guests who have received their final dose of an approved COVID-19 vaccine at least 14 days prior to the beginning of the cruise and have proof of vaccination. Here are the COVID-19 Guest Protocols currently planned which are subject to change as further details are established. They will be updated in accordance with guidance from public health authorities. View our health & safety protocols for more information. 

Featured Tropical Caribbean Cruise Ports

See Details

Half Moon Cay, Bahamas

Have the place to yourself at Half Moon Cay, our private Bahamas island. This crescent-shaped slice of paradise has won Porthole Cruise Magazine’s Best Private Island award for 20 years in a row. Rent a cabana and relax or take a dip in the aqua lagoon.

See Details
See Details

Key West, Florida, US

The beloved island of bohemians and adventurers, Key West has it all, from candy-colored houses, expansive outdoor eateries and plenty of boating, diving, and fishing excursions. Plus, manatees.

See Details

Featured Tropical Caribbean Shore Excursions

Introducing Our Newest Ships


Feel like you’re on “island time” on and off the ship—travel to the Caribbean aboard this new addition to our fleet. Rotterdam puts music front and center and creates the soundtrack to your Key West and Caribbean discoveries.

Nieuw Statendam

Cruise the Caribbean aboard the Nieuw Statendam, a modern beauty with dramatic spaces. Experience perfect bliss and more room as you’re carried to the Caribbean on this perfectly mid-sized ship.