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Off-Season Caribbean Getaways

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Dreaming of a beach paradise getaway without the price tag? Head to the Caribbean during summer or fall. Yes, it's also hurricane season, but many destinations, like Jamaica and Turks & Caicos, can go decades without a direct hit. Take out trip insurance when booking, then if a storm interrupts your holiday, the investment is protected.) So, go ahead, dream of white-sand beaches, azure water, and posh hotels with deep discounts.
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Port Antonio, Jamaica
For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas...
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Grace Bay TKCA 1ZZ, Turks and Caicos Islands
The centerpiece of Turks and Caicos is Grace Bay, on the island of Providenciales (known locally as Provo), where the miles-long sugar-sand shore routinely tops "best beach" lists for the Caribbean and the world. The inland area along this...
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One of the few hotels on picture-perfect Grace Bay Beach that can work for both honeymooners and families, Seven Stars sits on 22 acres of lush grounds at the edge of Princess Alexandria National Park and has studio to four-bedroom plantation...
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Enterprise Coast Road, Oistins, Barbados, Barbados
One of the best spots in the Caribbean for surfing is Barbados. And if you're not one of the best surfers in the world (like me), one of the best breaks on the island to catch some waves has got to be Freights Bay. The added bonus is that most...
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Carlisle Bay, Barbados
Carlisle Bay Beach is a beautiful crescent of sand just south of the urban center of Bridgetown. Hotels like the huge Barbados Hilton and the all-inclusive Almond Beach Club & Spa empty their vacationers onto her sand, cruise ship buses add to the...
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Val Des Pitons Forbidden Beach La Baie de Silence, St Lucia
For a taste of Miami by way of St. Lucia, look no further than Sugar Beach. Set on a white-sand crescent between the Piton mountains—within a 100-acre former sugar plantation studded with shady palm trees—the resort’s...
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Near the northern end of Andros Island, less than 15 minutes by air from Nassau, Kamalame Cay is worth visiting just for its remoteness from busy everyday life. But this 96-acre private island has other attractions, too: a scattering of 34...
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One Ocean Drive, Nassau, The Bahamas
When old money comes to Nassau's Paradise Island, The Ocean Club is where it prefers to stay. That's the way things have been since 1962, when the serenely posh resort opened along a dazzling stretch of sand known as Cabbage Beach. The 105-room...
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Harbor Island, The Bahamas
Harbour Island is an out island of the out island Eleuthera in the Bahamas. Home to a scant 1,500 people and more golf carts than cars, Harbour Island is the perfect place to get away from it all. It’s also home to the rich and famous who visit...
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Trinidad and Tobago
A gorgeous beach. Great local shops. Cool music. An international crowd. A great hang out and a very cool Tobagan chill!
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John F Kennedy Boulevard Bay, Curacao, Curaçao
The Curacao Marriott is currently closed for renovations. It is slated to reopen in late 2018.

The Curacao Marriott Beach Resort may be one of the best located hotels I’ve ever been to. Situated on a private beach in Piscadera Bay, the...
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Barnes Bay, West End 2640, Anguilla
While Four Seasons might have spruced up the property slightly when it took over management from Viceroy in 2016, the original clean lines and sharp angles of WATG's midcentury modern architecture coupled with Kelly Wearstler’s...