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400 Wall St, Key West, FL 33040, USA

Key West is billed as "the Home of the Sunset," which means every time the sun sinks below the horizon, it’s time for a party. Since the 1960s, Mallory Square’s dock has been hosting this nightly celebration, which begins two hours...

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Old road, Antigua and Barbuda
Opened in 2003, Carlisle Bay is set on a lush, isolated section of Antigua’s south coast and has a 21st-century design that feels more contemporary than Caribbean. With muted shades of grays, whites, and greens, the hotel projects an...
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West Bay, Cayman Islands
Grand Cayman outfitter Spirit of the West adds an extra thrill to its horseback-riding adventures. Caymanian owner Paul Rivers leads guests on a nearly two-hour trot along Barkers Beach, one of the island’s most secluded spots. After working up a...
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105 Calle de La Fortaleza, San Juan, PR 00901
I think the most appealing aspect of Old San Juan is the architecture and design of the city. Residential apartment buildings have been converted to designer boutiques or little B&Bs, and interior courtyards invite hungry guests to relax and...
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27 Calle Benitez Castano, Vieques, 00765, Puerto Rico
Vieques is all the things you heard about it. Quiet, quant, low key, and beaches you must venture to. My favorite was Playa Negra. It has black fine sands and solitude. This photo was taken in Isabel Segunda (a small town near the ferry port)...
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Mosquito Bay Beach, Vieques 00765, Puerto Rico
At Mosquito Bay Beach—also known as Starfish Beach—on Vieques Island in Puerto Rico, you'll find tons of colorful starfish. While the beach itself is small, it's still beautiful and perfect for a scenic walk. You won't get bored searching for sea...
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Esperanza, Vieques 00765, Puerto Rico
Esperanza is located on the southern side of Vieques island with a laid-back vibe reminiscent of Key West. This small town has an main street that runs parallel to the ocean called "El Malecón" that is dotted with friendly guest houses, funky bars...
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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...