After cruising the Caribbean more times than I can honestly count, Melissa and I have developed some pretty strong opinions about which ports are absolutely worth going ashore for — and which ones you might be just as happy to enjoy from the pool deck with a drink in hand.
Caribbean cruises typically stop at anywhere from three to seven ports depending on the length of your itinerary. Every port has something to offer, but if you want to get the most out of your time ashore, knowing what each port does best makes a huge difference. Here are our favorites.
St. Thomas, U.S. Virgin Islands
If you only get to stop at one Caribbean port in your life, make it St. Thomas. The harbor at Charlotte Amalie is one of the most beautiful in the Caribbean, and the combination of duty-free shopping, incredible beaches, and breathtaking hilltop views makes it almost impossible to have a bad day here.
Our top recommendation: take the aerial tramway up to Paradise Point for a panoramic view of the harbor and the islands beyond. Then head down to Magens Bay — consistently ranked as one of the most beautiful beaches in the world. You won't be disappointed.
Cozumel, Mexico
Cozumel is a snorkeler's and diver's paradise. The Mesoamerican Barrier Reef that surrounds the island offers some of the clearest, most colorful water you'll ever put a mask into. Even if you've never snorkeled before, Cozumel is the place to try it — the reef is shallow enough for beginners and stunning enough to make experienced divers do a double-take.
Beyond the water, the colorful streets of San Miguel are worth exploring. Grab some tacos from a local spot, browse the artisan markets, and pick up some vanilla extract and hot sauce to bring home. Cozumel is one of those places where the ship feels far away the moment you walk off the pier.
Nassau, Bahamas
Nassau is one of the most frequently visited Caribbean ports — and for good reason. It's close enough to the U.S. that even a 3-night cruise can make it there, and the combination of beautiful beaches, culture, and activities makes it endlessly replayable.
If you've been to Nassau before and done the downtown tour, consider booking a day at Atlantis on Paradise Island — it's a full resort experience with waterslides, aquariums, and beaches that can fill an entire port day. For something quieter, Cabbage Beach on the north end of Paradise Island is one of our favorite low-key beach spots in all of the Caribbean.
Grand Cayman
Grand Cayman is where you go if you want to swim with stingrays. Stingray City — a shallow sandbar about 30 minutes from port — is one of the most unique wildlife experiences in the Caribbean. You'll wade out into waist-deep water and be surrounded by friendly southern stingrays that glide past your legs and eat squid right out of your hand. It sounds terrifying. It's actually magical.
Seven Mile Beach is also right here, and it lives up to its reputation. Crystal-clear calm water, powder-white sand, and easy access from the cruise pier make it a top spot for a beach day. George Town has great duty-free shopping if you're looking for jewelry or rum cake to bring home.
St. Maarten
The dual-nationality island of St. Maarten (Dutch side) and Saint-Martin (French side) is one of the more culturally unique stops in the Caribbean. In a single day, you can have breakfast on the Dutch side, cross the border for a French lunch in Grand Case (one of the best food towns in the Caribbean), and be back at the beach by afternoon.
Orient Beach on the French side is stunning and offers beach bars, water sports, and a relaxed, European vibe. Maho Beach near the Dutch airport is famous for low-flying planes — the runway literally ends at the beach, and jets fly just meters overhead as they land. It's a spectacle unlike anything else.
Pro tip: Always book shore excursions in advance, especially for popular stops like Stingray City in Grand Cayman and Magens Bay in St. Thomas. Spots fill up fast, and cruise line-sponsored excursions are guaranteed to get you back to the ship on time — which matters more than you'd think.
Our Bottom Line
Every Caribbean port has something special to offer, and no two cruises are exactly alike. The best port days are the ones where you have a plan — even a loose one — and the flexibility to let the destination surprise you.
If you're thinking about booking a Caribbean cruise and want some help picking the right itinerary for your interests, reach out. This is literally what we do — and we love every minute of it.
