Toppa Top 10: The Ten Best Caribbean Beaches

Words by LargeUp Crew—

It’s that time of year again. The days are growing shorter, the temperatures colder, and whatever faint traces of summer  lingered through September and October are now, like summer itself, just memories. If you’re stuck in the cooler climes, this is your reality, and your mind is naturally starting to conjure thoughts on how to make your escape back to the beach. Well, we’re on your wave too, but, if you’re like us, not just any plot of sand will do.

We’ve put in a lot of time on beaches over the years and have developed the picky taste of true connoisseurs (ok, addicts). Our favorite sandtraps may be a little further off the beaten path than Frommer’s or the NY Times, but they’re worth the hike. As always, feel free to tell us what we missed, where we went wrong, etc. There’s always room for a do-over where beaches in the Caribbean are concerned.

Here are our picks, with no particular regard to order.

10. Treasure Beach, Jamaica

Jamaica is full of beautiful beaches—we have to given an honorable mention to Frenchman’s Cove out in Portland—but this hidden gem on the balmy South Coast might just take the crabcake. We recommend grabbing a drink at the Pelican Bar (pictured above).

9. Isla Margarita, Venezuela

Rated as one of the best beach towns in the world, this island between Venezuela’s mainland and Trinidad actually has several world-class beaches to choose from, spread across 106 miles of coastline. Playa Puerto Cruz and Playa El Agua are the most popular with tourists but Playa El Yaque is the best spot for windsurfing and La Galera may be the most stunning visually.

8. Wilderness Beach, Puerto Rico

Near Aguadilla and even closer to Isabella, you have to drive through a golf course to get to this lush spot (feel free to pick some mangoes as you go) and then up a beautiful dirt road under the shelter of tall trees. When you get to the shore, there will be about 20 cars parked (mostly SUVs and station wagons) and about 20-odd surfers in the water riding a gorgeous pipeline. This beach is on the hush-hush–strictly for the adventurous.

7. Orient Bay, St. Martin

Orient Bay (it’s sometimes called Bikini Beach, after a popular local bar) might not have the novelty of planes flying low overhead like Sunset Beach on the island’s Dutch side, but this gem on the French side has just about everything else—music, bars, eclectic beachgoers and plenty of flesh on display (part of the beach is designated for nudity).

6. Playa Flamenco, Culebra, Puerto Rico

Known as Ultima Virgen–the last virgin–Culebra is really the very last link in the Virgin Islands chain but administratively speaking is part of Puerto Rico. Playa Flamenco is the most beautiful on an island of beautiful beaches and is often rated as #1 or 2 in the world. Sorry, Thailand.

5. Trunk Bay, St. John

Perfect clean water, check. Hardly anyone there, check. Haffi take some crazy twisted steep hills that require radical gear shifting and expert driving, check.

4. San Pedro Beach, Ambergris Caye, Belize

Nearby Caye Caulker and Jaguar Reef both have their appeal but Ambergis Caye—and San Pedro Beach in particular—definitely takes the cake among Belize’s beach crop. For starters, getting there can be an adventure in itself, with many choosing to arrive by helicopter from the mainland. For another, it’s located just off the world’s second largest barrier reef.

3. Cabo San Juan (Tayrona National Park), Colombia

A perfectly hidden cove surrounded by virgin jungle, Cabo San Juan is not your typical resort beach with perfectly calm water. The bowl-like shape of the sheltered inlet makes it less of a natural swimming pool and more like a natural wave pool or sauna, making it difficult to stand or swim but perfect to just rock hypnotically back and forth. Its biggest liability as a tourist destination is actually its greatest asset; as part of the Tayrona National Park it is completely undeveloped and is not even accessible by car. It’s about an hour’s hike from the eco-habs and cabanas in the interior of the park, which are accessible only on horseback over muddy jungle-mountain paths from the reception area. Which is accessible only by jeep from the entrance of the park. Which is accessible only by local bus. Or you could swim there and just hang your hammock on the gazebo, situated on the point which juts out into the Caribbean.

2. Pigeon Point, Tobago

When we vacation, we go to Trinidad for carnival. This is where the people who live in Trinidad go to vacation. Nuff said.

1. Playa Cabarete, North Coast, Dominican Republic

The North Coast of the Dominican Republic is one of the best kept secrets in the Caribbean. The pristine waters and winds host choice conditions for basically all extreme watersports. Playa Cabarete is a top destination for one of the hottest new trends–kitesurfing/boarding–as well as windsurfing, stand-up paddle and–most of all–plain old surfing. Part of the attraction is the proximity to nearby Encuentro Beach and Kite Beach, which boast perfect conditions for surfing and kiting, respectively. For the less adventuresome, Cabarete’s also got the whole picturesque beauty thing, too.