Tropical Caribbean Cruises

Tropical Caribbean cruises to Key West are ideal as a family cruise or a romantic adventure. Several literary legends have called the island home, most notably 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. Every tropical Caribbean cruise to Key West includes a day at Half Moon Cay, our top-rated private island in the Bahamas. Grand Turk and Amber Cove are also featured on these itineraries.

Featured Tropical Caribbean Cruise Destinations

Let loose in our tropical Caribbean destinations. Experience the laid-back vibe of Key West or the thrilling waterparks of Amber Cove. You’re never too far from a frozen drink and a sandy beach.

People horseback riding in the surf on Half Moon Cay, Holland America's award-winning private island

Half Moon Cay, Bahamas

Our 2023-2024 Caribbean cruises celebrate 26 years of Half Moon Cay. Every tropical Caribbean cruise to Key West includes a day at this award-winning island. Cool down with cocktails, stroll the white-sand beach or cycle the bay on a water bike.

View of a pier on the water in Key West, Florida

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.

Grand Turk

Grand Turk

Known for its natural wonders, a day on reef-ringed Grand Turk is truly a day in paradise. The island’s beaches are a serene escape, while under the surface bustles with marine life.

Amber Cove

Amber Cove

Amber Cove in the Dominican Republic is the best of both old and new. You can find 15th-century historical sites along with modern resorts and waterparks.

Featured Caribbean Cruise Itineraries

Featured Tropical Caribbean Shore Excursions

Find a vast selection of tropical Caribbean shore excursions. Take a luxury catamaran sail on the ocean or a nature kayak through Key West’s mangroves, where you might spot a manatee.

Your Sanctuary At Sea


Music is at the heart of Rotterdam, our newest ship with Music Walk®, an exclusive collection of live music performances. You’re in for a treat as you cruise the tropical Caribbean with exquisite cuisine, award-winning service and more.

Nieuw Amsterdam

Nieuw Amsterdam celebrates historic New York City with an inspired design and renowned art collection. While not relaxing in your sumptuous stateroom, dine in your choice of specialty restaurants or pamper yourself at the Greenhouse Spa & Salon® retreat.

Nieuw Statendam

Luxuriate in a welcoming retreat with dramatic light-filled spaces on board Nieuw Statendam. Enjoy perfect bliss and more room to take in the view as this award-winning ship carries you to tropical Caribbean islands.

Caribbean Cruises

Explore the Caribbean on perfectly sized ships where you always have a sunny corner to call your own. Uncover perennial favorites on convenient 7-day roundtrip cruises or visit the region’s distant reaches, such as the Panama Canal on longer journeys.