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Which Caribbean Island Are You?

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    The Relaxation Specialist: Aruba

    En español | You’re spoiled for choice when it comes to a day at the beach in the Caribbean; most islands there boast super stretches of sand. But for calm waters and reliably sunny days (the most in the Caribbean, the tourist board claims), it’s hard to beat Aruba. The Dutch island is home to picturesque, powder-white Palm and Eagle beaches, as well as the aptly named Baby Beach, lapped by calm and shallow waters that welcome even the most timid bather. Aruba, which lies outside the hurricane belt and receives very little rainfall, is popular with the 50+ crowd.

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    The Shopper: St. Thomas

    Bring an empty suitcase (or two) to this duty-free mecca. Havensight Mall, just a credit card toss from the cruise pier in the capital of Charlotte Amalie, sells cameras and Rolex watches, liquor and local crafts. Pick up Waterford crystal and art at the boutiques lining downtown’s Main Street. Merchandise ranges from pricey diamond necklaces to modest hand-embroidered tablecloths. Bargain where you can — but don’t expect to at upscale Yacht Haven Grande center, which sells fashions by Gucci, Louis Vuitton and White House | Black Market.

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    The Wallet Watcher: Dominican Republic

    The Dominican Republic, which shares the island of Hispaniola with Haiti, is known for its all-inclusive beachfront resorts that suit any budget. In Puerto Plata, less than $100 a person daily buys a comfy room with all the food you care to eat and all the booze you can safely quaff. In more upscale Punta Cana — where resorts line miles of wide white-sand beaches — you’ll find budget lodgings with spacious rooms, swim-up bars and groaning buffets. At the opposite end of the spectrum are Vegas-style resorts replete with casinos, butler service and fine-dining restaurants. 

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    The Romantic: St. Lucia

    Picture a dreamy tropical island: Beaches fringed by palm trees. Lush vegetation. Brightly colored parrots. Jagged mountain peaks. St. Lucia delivers all that and more, as well as a range of resort experiences, from affordable inns to once-in-a-lifetime splurges. If you’re into fitness or golf, followed by soothing spa treatments that are built into the (not cheap) room rates, the award-winning, all-inclusive BodyHoliday awaits.

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    The Hedonist: Jamaica

    Hypnotic reggae music, historic plantation “great houses” and the laid-back attitude of residents speaking a lilting local dialect draw music lovers, history aficionados and pleasure seekers alike. For the uninhibited, the aptly named Hedonism II resort hosts revelry in the buff. Whether you’re being serenaded with Bob Marley songs by a resort band, fending off (or encouraging?) the ubiquitous ganja vendors or watching daredevil cliff divers with a frosty Red Stripe in hand at Rick’s Café in Negril, “every little thing gonna be all right.”

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    The Sophisticate: Saint Barthélemy

    Over Christmas and New Year’s, supermodels and A-listers are spotted on yachts on this elegant island, which is part of France. Expect to shell out 100-plus euros a person for dinner at chic restaurants in the capital of Gustavia. That doesn’t mean you can’t munch a cheeseburger in paradise; Jimmy Buffett is one of the famous folk who patronize Gustavia’s simple Le Select café. You know you’re on a French island (commonly called St. Barth or St. Barts) when vacationers casually stroll au naturel on secluded Grande Saline Beach. Rentals can be cheaper than hotels; check out Wimco Villas, among others.

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    The Nature Lover: Dominica

    Billing itself as “the Nature Island,” this unspoiled volcanic gem attracts those in search of the less developed Caribbean. It boasts about 300 miles of hiking trails, notably the Caribbean’s first long-distance hiking path, the 115-mile Waitukubuli National Trail. Dominica is also known for superior diving. You can snorkel or scuba in submerged craters, including the “Champagne Reef,” where water warmed by geothermal vents bubbles up around you. Boiling Lake, reached by foot, is too hot for swimming. Less intrepid visitors can walk in a rain forest and snap photos by a cascading waterfall.

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    The Split Personality: Saint Maarten/Saint Martin

    This half-Dutch, half-French island fulfills multiple vacation desires. The Dutch side appeals to those looking for bargain diamond jewelry or a bit of luck at the casino. The French side offers excellent restaurants and shops in its capital, Marigot, as well as Orient Beach, more than a mile long and one of the best in the Caribbean. Lined with hotels and cafés, it attracts nude sunbathers, along with those who prefer to keep their swim togs on. Indeed, clothing is optional throughout the family-friendly Club Orient resort — even in its restaurants.

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    The Adventurer: Cuba

    With the Caribbean’s largest island opening up to travelers from the United States, Americans are flooding in. Glitches with reservations and transport still occur, however, so it’s easiest to take an organized trip. Independent travelers can stay in Airbnb-style accommodations, called casas particulares, via trips they book on their own. Independent travel likewise allows you to meet locals, dance ’til dawn at music clubs and sample — and bring home — Cuban cigars. U.S. airlines fly in and will arrange visas. Note, though, that pure tourism is still illegal. Your trip must officially be for “people-to-people” interaction or some other authorized purpose. 

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    The Commitment Avoider: A Cruise

    Caribbean cruise can give you a taste of multiple islands. It’s also great for multigenerational getaways, with nonstop activities for children and adults. Not the cruising type, you say? Don’t be so sure until you weigh the other benefits. Cruises can be as short as three days, and the constant change of scenery means you needn’t spend time in a vacation spot that’s not right for you. Then there’s the veteran traveler’s unique joy: unpacking just once on vacation. And if a cruise introduces you to that special isle that suits your style, you can always visit it next time by air.

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