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San Juan-Caguas-Guaynabo, PR, Puerto Rico
Cuevas del Indios (Indian Caves) of Arecibo offers a tidbit of ancient history of a lost people. An easy-to-find natural wonder, with a simple $2 fee for parking, this you won't want to miss. Bring some sunscreen and your camera. Begin your hike...
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Val Des Pitons Forbidden Beach La Baie de Silence, St Lucia
Sugar Beach Viceroy Resort is one of those dreamy beach havens where luxury is standard. Overall the best hotel on the island of St.Lucia for amenities, location, activities and dining options. Driving along the jagged roads of St. Lucia, from the...
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Scrub Island, VG1120, British Virgin Islands
The 2-year-old Scrub Island Resort has one of the closest marinas to the North Drop, a famous fishing spot for blue marlin. Half- and full- day fishing charters include a boat, a guide, and equipment. Guests who land a tuna or a marlin can bring...
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Baie de Saint Jean, Saint Barthélemy 97133, St Barthélemy
Every place has a history & Eden Rock is no exception. Dating back to the 1950s, Eden Rock was the first hotel built on St. Barth, before the island was even a travel destination. At the time, Eden Rock was a guesthouse, a sanctuary for those...
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A trip to Barbados inspired Joe Poulin to launch Luxury Retreats in 1999. Since then, the company’s portfolio has grown to more than 2,000 properties in 50 destinations, including 17 in the Caribbean. Poulin has a villa for every taste and every...
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PR-458, Aguadilla Pueblo, Aguadilla 00603, Puerto Rico
One of my favorite dive sites on the west coast of Puerto Rico is Crashboat in Aguadilla. This shore dive is easily accessible for all levels of diving, and you're guaranteed to see something amazing on this artificial structure. Crashboat is...
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Cow Wreck Beach Bar on Anegada has, in my book, replaced Jost Van Dyke's Soggy Dollar Bar as the most beautiful and remote destination in the British Virgin Islands. This beckoning hammock can be found alongside the bar. Though the few visitors...
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Calle Poblado Marinero, s/n, 38683 Los Gigantes, Santa Cruz de Tenerife, Spain
Few things are more thrilling when travelling than exploring the vast waters of the ocean, and swimming along its colorful and surprising wildlife. And in Tenerife, the best place to live this experience is with the Los Gigantes Diving Centre,...
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142 Calle Flamboyan, Vieques, PR 00765
Just sayin'... As far as beach bars go, this town's one-street scene is all bananas. After my trip, I called one of my awesome friends from college (go Providence!) who has frequented Vieques for work (lucky her), and when I told her how shocked I...
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6000 Rio Mar Blvd, Río Grande, PR 00745
Rented 4WD needed for roads out to Green Beach, but worth the adventure. Very private and completely gorgeous. Great snorkeling too.
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Sec Gozalandia, San Sebastián 00685, Puerto Rico
As with many other natural wonders in Puerto Rico, there isn't a clearly defined marker. Normally, to find Gozalandia, you would first have to visit it with a local, because getting directions there can be complicated. Lately, there is talk...
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San Juan-Caguas-Guaynabo, PR, Puerto Rico
This is my favorite hike by far. Cueva Ventana ("Window Cave") is a beautiful, scenic hole in the side of a mountain that opens up to a lush, green valley down below. You'll trample through mud, hunker down under low-hanging stalactites, dodge...
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The beauty of the island doesn't get more mesmerizing than this!! Head over to Charco Azul in the north of the island in Vega Baja. Bring lunch and plan to stay for a while! Photo by Gerald Giovanni
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Playa Sucia, Cabo Rojo, Puerto Rico
Five years ago, my friends and I found a secret beach near the Cabo Rojo Lighthouse. To this day, we've never seen anyone else there. Ignore the beach's misnomer—Bahia Sucia (dirty bay)—and plan on an 8 a.m. to 8 p.m. outing to this natural...
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ROUTE NATIONALE, PIGEON 97132, Guadeloupe
Plage Anse Thomas is a petite-pebbled beach located in the south of Bouillante on the island of Basse-Terre. It is a secret spot for locals and often uncrowded. What makes this tiny gem so special? It is the site of one the many natural hot...
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Nevis Peak, the towering bulge rising from the middle of the island, can be hiked alone or with a guide. If you’d rather explore with a professional, go with Lynell E. Liburd of Sunrise Tours. He’ll lead you on a strenuous hike to the...
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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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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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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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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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Dominica
Sip a passion fruit punch at this small beach hut beside Soufrière's splendid Roman Catholic Church, Saint Mark, built in 1880. Then hop in the homespun sulfur soaking pools on the shoreline. A fumarole warms the sea water and injects bubbles into...
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Dominica
Geothermal springs on the ocean floor release curtains of bubbles at one of the world's most famous and unusual dive sites. Shallow enough for snorkelers and folks new to scuba, this spectacular reef has lavish sea life, from sponges to parrotfish...
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Emerald Pool Trail, Dominica
Stroll 15 minutes down through a lush rainforest to a gorgeous 40ft (12m) waterfall grotto. Railings and a broad, well-maintained trail make this trip accessible even to non-hikers. Located in the World Heritage Site of Morne Trois Pitons National...
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Unnamed Road, Calibishie, Dominica
Swoops of smooth, scarlet earth overlook the northeast coast at Point Baptise near Calibishie. A mile-long coral reef protects the village's seashore, creating a calm lagoon. But the Atlantic erodes and slaps waves high onto the dramatic headland....
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Wotten Waven, Dominica
The proprietor, Screw, a charismatic Rasta also known as "Irie Man," has spent years building this colorful open-air retreat, just a 20-minute drive east of the capital Roseau. Slip into six pools of varying temperatures on a lush, leafy hillside...
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Paillotte Road, Dominica
An easy 10-minute trail leads to paired cascades on the west side of the mammoth Morne Trois Pitons National Park: the higher, lefthand Father (279ft/85m) and the smaller Mother (131ft/40m). While the fun officially stops at the viewing platform,...