There are many reasons to cruise the Caribbean with Holland America Line, from flexible itineraries to our award-winning private island Half Moon Cay. With so many options, how do you choose which Caribbean cruise to go on to experience island magic, sun-kissed beaches and paradise-packed itineraries? Let’s explore the places you can cruise to in the Caribbean and the best times to take a Caribbean cruise:

When to Cruise to the Caribbean

When you’re looking to escape the summer heat, a coolcation likely tops your list. However, if you prefer margaritas and beach wear over pumpkin lattes and winter gear, consider taking a Caribbean cruise during the fall and winter. Book a Caribbean cruise that works with your schedule, from a 4-day trip to the Bahamas to a 35-day Caribbean journey. There are plenty of options to choose from with Holland America Line. Our Caribbean cruises set sail from October through April.

Another perk of cruising to the Caribbean during the winter? Holiday vacations! Why not leave the cooking and cleaning to us as you celebrate the holidays, escaping the winter snow and cooler temperatures so you can bask in the warm sunshine.

Where to Cruise in the Caribbean

Eastern Caribbean

Experience the beauty of the Eastern Caribbean as you island hop in destinations like Turks & Caicos, Puerto Rico, St. Thomas and Half Moon Cay. Soak up the sun on white sandy beaches. Snorkel among tropical fish in crystal clear blue waters. Explore a 17th-century fortress in Puerto Rico or go horseback riding on Half Moon Cay’s shores. There’s plenty to do in the Eastern Caribbean, whether you’re looking for adventure, romance or just pure relaxation.

Southern Caribbean

When you embark on a Southern Caribbean cruise, prepare for an incredible getaway to places like Aruba, Bonaire and Curacao. Explore Aruba’s wind-sculpted terrain and coastal cliffs with cacti. Enjoy views of Bonaire’s reefs and flamingos. Take in the beauty of rainforests in the Dominican Republic or snorkel off its coast with an underwater scooter. Plus, look forward to visiting our own piece of paradise on Half Moon Cay.

Tropical Caribbean

Love the look of swaying palm trees and shimmering waters? Though you’ll see this throughout the Caribbean, you’ll soak up these views in the Tropical Caribbean, where you’ll also find sunset parties at Mallory Square and live music on Duval Street in Key West. If you’re a fan of literary legends like Ernest Hemingway and Judy Blume, then you may discover what inspired them to call Key West home. The Tropical Caribbean also includes a day at Half Moon Cay, and you may find Grand Turk and Amber Cove on the itinerary as well.

Western Caribbean

Visit some of the top waterfalls in the Caribbean, like Dunn’s River Falls and the Ocho Rios Blue Hole in Jamaica. Take a Western Caribbean cruise to the Cayman Islands and explore some of the area’s shipwrecks. Soak up the views at historic landmarks, like Chichén Itzá, a UNESCO World Heritage site in Cozumel. Bask in the beauty of island beaches and sunshine, including a stop at Half Moon Cay.