The Best Secluded Shores of the Caribbean

The start of the path is quite easy to find in Friar’s Bay. Just walk North past Kali’s Beach Bar and past Friar’s Bay Beach Bar until you see a path marked by orange arrows. It should lead up a hill. (There appears to be another path that goes around the rocks lower down, but I wouldn’t recommend taking that one.) Once you crest the hill, the still somewhat clearly marked path opens wide in all directions. You get a clear view of the ocean on your left and grassy hills on your right. Cross through a fence. Walk past some old ruined condos. Meet up with a road. Wait, a road? I could have driven here? Yeah, well… the walk is pleasant and you’re at Happy Bay before you know it. And talk about “happy”! This secluded bay is often almost devoid of the throngs which plague some St. Martin beaches like Orient Bay. Here, there are practically no facilities (though they have been talking for a long time about adding some) so it just doesn’t attract crowds! It’s not as expansive as my favorite beach on St. Maarten (Long Bay) though… Anyway, once you take your pick of the many excellent spots to spend the day on this beach, it’s just a matter of deciding how much you’re going to take off. ;-)

Many islands have laws with steep fines against wearing beach wear when not on the sandy shoreline and while you may have heard of folks going au-naturel on St. Martin, that’s certainly not the norm throughout the region. On St. John, however, things were a little different. About a mile walk from a parking lot on the edge of Cruz Bay along what’s called the Lind Point Trail, through typical island bush and over a hill and down through more bush past a fork (where either choice gets you to the same place) intrepid travelers are rewarded with a tiny strip of sand, only around 25 yards long, unofficially known as the island’s only nude beach: Salomon Beach. I’ve been to this secluded sandy alcove a number of times and without fail the maximum number of sun worshipers was never above four or five. In fact, most times, the beach was deserted. So, for years this is where those with a passion for enjoying nature to the fullest could go to let it all hang out in relative privacy… Until recently. Since my last trip to Salomon Beach back in 2007, there’s been a crackdown on this unofficial naturist haven. Suddenly being a free spirit isn’t so free due to the stiffness of fines—around $110 for those caught with their pants down (so to speak). But, hey, doesn’t mean you can’t press your luck!

Pictured is Siete Mares Playa (or Seven Seas Beach) in Fajardo, Puerto Rico—a sneaky strip of sand and local favorite that hides not one, but two semi-private playas off the beaten path. On the far left side of the beach you can find an enticing little path into the mangroves. Follow this for a bit and you’ll get to a fork. Take the path on your right. You’ll then come to another fork. Again, take the path on the right. After about ten minutes, you’ll come to a sign for Playa Colora—your first secluded beach! Once you’ve soaked up some sun (and rum) on your first private beach, just head back to the path. Take your first right and walk for about five minutes. The path will break through the mangroves onto another orangey colored beach named Playa Escondida (or Hidden Beach). If it’s got “hidden” in the name, it’s got to be secluded, right?

Known as the “Jewel in the Crown” of the Southern Grenadines, Tobago Cays Marine Park comprises five picture-perfect, uninhabited islands surrounded by a clear lagoon. Here, you’ll find sea turtle nesting sites and feeding areas, small systems of mangroves, and the most well-developed coral reef complexes in St. Vincent. Swim with the resident turtles, snorkel around the almost 2.5-mile-long Horseshoe Reef, or simply relax on a magnificent white-sand beach—each island has at least one.

One of Anguilla’s most secluded beaches, Little Bay is tucked beneath a series of bluffs on the island’s northwest. Usually reached by boat or kayak from Crocus Bay, this tiny, undeveloped stretch of sand hugs a cove with calm turquoise waters filled with small tropical fish, sea turtles, and starfish. Bring drinks and snacks, rent gear from Da Vida Restaurant, and kayak (or boat taxi) over in the morning to avoid the crowds and spend a couple of blissful hours away from it all.

Pristine, untouched and unforgettable: There’s no other way to describe this natural park just off the northeast coast of St. Croix. Walking trails crisscross the expanse through frangipani and tamarind trees and cacti to beautiful beaches. Turtle Bay, on the western side, wows with its magnificent snorkeling; the protected waters and massive coral reef are home to more than 250 kinds of fish. Admission numbers are limited each day; advance booking is required.

Suppose I told you there was a small, remarkably idyllic and fairly unpopulated island in the Caribbean just a short distance from the mainland United States, an island so immaculate, plans were in the works to make it a National Wildlife Refuge, an island with a beach rated one of the best beaches in the world, an island where you could basically do whatever you wanted along its iridescent shores with little chance of being interrupted by prying eyes.... What’s the first thing you’d do? Well, if you were the U.S. military back in 1901 and the destination in question was the island of Culebra, you’d blow it all to hell! For nearly 75 years, bombs pounded Flamenco Beach on Culebra, la “Última Virgen,” while the U.S. military used it for target practice. Protests drove the Navy away, but some relics remain on the once pristine sands as a reminder of how never to treat one of the best strips of beach in the world. During the weekends, Flamenco Beach can get fairly crowded with “mainland” Puerto Ricans taking the ferry over for a day in the sun, so I recommend you make time during the week for a more secluded experience. There are vendors nearby, but not too near, to make your stay a pleasant one with local cuisine and plenty of ice-cold beer.

One of my favorite places in the whole world—Vieques! I’m actually a little apprehensive to share, because I’d love to keep it the semi-secret it is. If you time it well, you can have this beach all to yourself.

We were lying in the sand in Vieques. We’d been told to watch out for horses, but nothing could prepare me for this. What a majestic experience to see wild horses free on the sands of Sun Bay Beach.

This ex-Rockefeller estate originally opened as a hotel in 1964, and relaunched in January 2020, after a four-year closure and a multimillion-dollar renovation. Rosewood Little Dix Bay features a half-mile of powdery white sand on Virgin Gorda and offers a variety of accommodations from tree-house suites, to villas and beachfront cottages.