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The Best Secluded Shores of the Caribbean

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The best strips of sand under the Caribbean sun are the ones less traveled. The ones away from the throngs of tourists and all-inclusives. Here are a few of my favorite secluded beaches throughout the West Indies.
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I spent a year living in the Caribbean where as a local "resident" the standard Sunday Fun Day activity is a boat trip from the US Virgin Islands to Jost Van Dyke in the British Virgin Islands. The traditional stop along the way is at Sandy Spit...
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British Virgin Islands
This beach was one of my favorites in Tortola. I would likely say the same about every beach I've been to in Tortola so don't mind me. I will say, however, the mosquitoes are rampant as the sunset nears. Bring repellent! I also had a wicked Pain...
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Lee Road, Valley, Spanish Town, British Virgin Islands
This property is currently closed until late 2019 for hurricane-related repairs. 

Experience ‘voluntourism’ at Rosewood Little Dix Bay by joining the Association of Reef Keepers (ARK) and helping find and tag wild sea turtles....
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Playa Sun Bay, Vieques 00765, Puerto Rico
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.
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Puerto Ferro, Puerto Rico
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.
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Flamenco, Culebra, Puerto Rico
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,...
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What’s one of my favorite things to do when I go home to St. Croix? Literally beg one of my friends with a boat to have a Buck Island lime. There’s no better way to spend the day than casting off, heading north for a few minutes, and...
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Crocus Hill 2640, Anguilla
Anguilla has plenty of large, world-class beaches (many with equally alluring beach bars), like Meads Bay and Shoal Bay. But my favorite beach by far is the aptly named Little Bay Beach. This secluded, tiny strip of sand roughly 40 feet long is...
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Salmond, Barbados
Heading up north in Barbados is a great way to get away from the bustle of Bridgetown and the hustle of the west coast. And if you’re going north, why not go all the way to North Point? First off, Mondays are the best day for this excursion as...
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Petite Tabac is one of five tiny islets that make up the Tobago Cays archipelago in the Grenadines. Everything you could ever want in a deserted island paradise is here. You’ll find shallow, crystalline waters teaming with colorful sea life...
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Fajardo, PR, Puerto Rico
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...
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St John, USVI
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,...
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Happy Bay, St Martin
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...
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Woodlands, Montserrat
Montserrat, like many islands in the Lesser Antilles, is volcanic by origin and the island’s features are those typical of a volcanic island: steep hills, rich soil, and something many Americans have never experienced, black sand beaches. So,...
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Castara, Trinidad and Tobago
Pressed into the leeward side of Tobago between the sea and the steep rise up to the island’s mountainous Main Ridge spine, the tiny village of Castara offers intrepid travelers the essential aspects of the uncommon Caribbean. On the day we...