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Trip Ideas

Which Caribbean Island is Right for You?

In winter, the idea of escaping to a Caribbean island probably occurs to each of us at least once a day—and thanks to increased seasonal flights to the region, it’s never been easier to put that plan into action. The only challenge is deciding where to go. With more than 7,000 individual islands (and 28 different countries), there are lots of wide beaches and shimmering waters to choose from. Here, we do some match-making to help you out.

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For Foodies: Anguilla

With more than 100 restaurants packed into just 35 square miles, this low-key island has rightfully earned its rep as the culinary capital of the Caribbean. To experience the best over-the-top meals, don't miss CuisinArt, where an on-site hydroponic farm provides fresh ingredients daily for the hotel's various restaurants, which range from a Mediterranean café to an authentic Japanese teppanyaki and omakase. JS Tip: Check out the weekly Chef’s Table food and wine pairing dinner with Chef Jasper Schneider or sign up for a cooking class. At the new Four Seasons Anguilla, the see-and-be-scene crowd heads to the Sunset Lounge for sushi, sashimi, and tapas—paired with fine champagne, aged rums, and Cuban cigars, while seafood lovers make the hotel's buzzy Cobà a must-stop on any island foodie tour. Opened in 1984 with a 2-Michelin star chef at its helm, the Malliouhana is credited with bringing fine dining to the island. Today, under the direction of NYC-import Chef Marc Alvarez, the resort serves a standout menu that highlights local flavors and ingredients, and has the island’s largest selection of rums from around the world; schedule a tasting with “rummelier” Albert Lake, who also oversees the resort’s 25,000-bottle-strong wine cellar. If you'd rather leave your resort, try local favorites Tasty’s Restaurant (get the steamed fish with root vegetables, or the conch stew and dumplings), the seafood-focused E’s Oven, or Ken’s Ribs and Chicken (open only on the weekends) for BBQ and ginger beer. As for popular food trucks, head to The Valley (we love Papa Lash’s for his famous plantain sandwiches), or hit waterfront spots like Jacala on Meads Bay (known for its whole grilled snapper and steak tartare), Robinson Crusoe for the johnnycakes, or Smokey’s at the Cove for the potent rum punch.

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For Outdoor Lovers: St. Lucia

St. Lucia is the perfect Carib getaway for outdoor lovers thanks to its gorgeous beaches, 100 acres of tropical rainforest, and the twin Piton Mountain volcanic peaks (a designated World Heritage Site) which watch over the island. You can explore the lush landscape in a variety of ways – a treetop canopy zip-lining tour, a hike through the Pitons, or, how about an ATV ride or drive in a four-wheel buggy around the Soufrière basin – one of the world’s only “drive-in” volcanos? The island has plenty of stylish resorts, but we recommend the all-inclusive The BodyHoliday, an integrative health and wellness hotel (which also serves alcohol and gourmet food!) that gets you outside for activities like yoga, beach bootcamps, and the one-mile Wellfit Trail, in which a number of fitness stations (think parallel bars, rope bridges, a tire run, and more) are set along the beach and up into the surrounding hills. If you’re more of a thrill-seeker, the resort can also take you off-site to bike the coastline or abseil over a river gorge. At Sugar Beach, A Viceroy Resort, tour options include a half-day hiking/swimming adventure that brings you on a three hour climb to the summit of Gros Piton, followed by a swim in the sea—and a BBQ lunch—when you get back down. You can also arrange horseback rides and hikes to secret waterfalls, along with bike rides along jungle trails or through the ruins of an 18th-century French plantation.

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For Beach Bums: Antigua

There’s no shortage of stunning beaches in the Caribbean (after all, that's the region's biggest draw), but if you’re a die-hard fan of the three S’s (sun, sand, and surf), then Antigua’s your place. The island has 365 beaches—one for every day of the year, as locals say with pride— most being tucked away in protected coves with calm lapping waters. So where do you start? If you don't mind the crowds, head to the more developed northwest coast, to spots like Dickenson Bay or Runaway Bay, Fort James beach (popular with locals), and surfer-favorite Galley Bay. If you visit the four crescent-shaped beaches of Hawksbill, be ready to see some bare bodies as one of the stretches is clothing-optional. Head southeast and you'll find the beaches of Half Moon Bay—a designated national park—and Long Bay which are ideal for families. Meanwhile, adventure-seekers should navigate the rougher roads of the south-central coast to reach the beaches around Rendezvous Bay. As for where to stay? Check into the Blue Waters Resort, lush with acres of tropical gardens, freshwater swimming pools, and access to several secluded beach coves. Jumby Bay, A Rosewood Resort, is also worthy of consideration. It offers a “Castaway Experience” that takes couples to the deserted Maiden Island for an afternoon of private beach time, complete with a made-to-order picnic and side-by-side massages.

RELATED: Secret Caribbean

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For Stylistas: St. Barts

A favorite among celebrities and the jet-set crowd, this 8-square-mile French island is undoubtedly the most fashionable in the Caribbean (as everyone – surfers, beach-hoppers, scenesters, etc. – makes dining out look like a runway). Make sure your resort wear wardrobe is on-point with a visit to some of the duty-free island's shops, which range from high-end to hip and homegrown. Set out on the harbor in the town of Gustavia, Quai de la République is considered the Fifth Avenue of St. Barts as it's lined with a wealth of luxury retailers like Bulgari, Louis Vuitton, and Hermes; some of which stock items not available in the U.S. (and may also have shorter waiting lists for hot-ticket pieces.) Rue du General de Gaulle and Rue de Roi Oscar II are two other popular shopping streets in town, while the Carré d’Or plaza – tucked off of the Quai de la République – features an array of indie designer boutiques, including the original outpost of Calypso St Barth. The village of St. Jean also has its share of trendy shops peddling boho-chic fashion and home décor, particularly along La Villa Creole near St. Jean Beach. With such a fashionable clientele, the hotels of St. Barts have upped their style game. Just opened in late-fall 2016, Villa Marie Saint-Barth features 18 bungalows and villas individually decorated by its French owners with furnishings sourced from around the world (see: Indonesian sculptures, Tunisian woven rugs, French metal-and-wood armchairs, and headboards covered in Diane von Furstenberg fabrics). The famed Le Guanahani recently underwent a $40 million refresh that resulted in a new custom furniture collection and all-new interior by Miami-based designer Luis Pons. Over at Le Sereno, guests stay in 36 breezy suites designed by Christian Liaigre. Upgrade to a villa and you'll even receive an exclusive Anya Hindmarch tote painted with a colorful map.

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For Big Spenders: Necker Island and Peter Island, BVI

If you’ve got $$$ to spend, you may as well blow some on a sunny getaway for you and your closest friends. Part of Sir Richard Branson’s five-star Virgin Limited Edition hotel collection, Necker Island, in the BVI, is a full-service, exclusive-use island hotel that’s bookable for just you and 33 of your closest squad members – once in, you'll have your run of the place, from the beaches to the restaurants, the Great House to the Balinese-style villas. A dedicated water sports team can organize snorkels, sails and more, a tennis pro can give you lessons, and spa therapists are on hand for ensuite massages. Also part of the British Virgin Islands, Peter Island Resort & Spa sits on an islet that was once inhabited by Christopher Columbus and the pirate Blackbeard. Since the 1960s, it’s been a private island resort catering to the deep-pocket crowd with plush ocean-view rooms, beachfront suites, and cliffside villas that are customized with all your favorite things, from snacks to music. Mingle with other guests at the stylish lounge, beachside grill, or gourmet restaurant; go kayaking or sailing; or simply relax on one of the five quiet beaches.

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For Romance Seekers: Mustique

Few Caribbean islands can match the ultimate hideaway set-up of Mustique, where 1,400 acres are home to just one full-service hotel and a collection of private villas. Located at the tip of the Grenadines (flights connect via Barbados), the lush private island was bought by an English Lord in the late 1950s, and soon became a playground for his jet-set pals, including Mick Jagger and Princess Margaret (and more recently, for privacy-seeking celebs like Prince William.) Today, visitors [can rent ]( of the 100 or so homes (the dedicated Honeymoon section of the rental website offers choices ideal for newlyweds), or check into the 20-room Cotton House, which has a top-notch restaurant and spa. Sunset cruises, horseback rides, tennis time, and water activities—including nighttime dives surrounded by glittering phosphorescence – can all be arranged. Our favorite to-dos: Macaroni Beach for a deluxe champagne picnic and Pasture Beach at moonlight to spy leather back turtles.

RELATED: 25 Incredible Caribbean Stays

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For History Buffs: Puerto Rico

Soak up the history of the second oldest city under U.S. jurisdiction – and the second-oldest European-founded city in The Americas – on a visit to Puerto Rico’s Old San Juan. Settled by the Spanish in 1521, the historic center of San Juan is actually a seven-square-block island connected to the rest of the city by a bridge, and lined with cobblestoned streets made of blue-hued adoquine. Over 400 restored 16th- and 17th-century Colonial-era buildings can be found throughout Old San Juan, from elegant residences to imposing defense forts like El Morro and the Castillo de San Cristobal. Wander around on foot, hop on the free Old Town trolley, or rent a bike to explore. Two hotels with historic cred: the beachside Condado Vanderbilt, which was opened in 1919 by Frederick William Vanderbilt, and recently emerged from a $200 million refresh; and set further from town (about 35 minutes from the airport), Dorado Beach, a Ritz-Carlton Reserve, located on 50 beachfront acres that once belonged to Laurance S. Rockefeller, who was a dedicated conservationist way before “green” was cool. Take a stroll along the 11-mile Rockefeller Trail, savor dishes by celebrity chef José Andrés at Mi Casa, or head to the stunning indoor/outdoor spa – one of the best in the Caribbean – for standout services like the Hammock Massage.

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For Families: Turks & Caicos

Not long ago, this archipelago southeast of the Bahamas was a lesser-known getaway frequented primarily by high rollers and incognito celebs (though you can still find plenty of those, too). In the last decade, however, a host of new resort developments and increased flight service from the U.S. has upped its profile—and made it more popular with, and affordable for, families. Wide, powdery, and perfect for building sandcastles, three-mile-long Grace Bay Beach – lined with hotels that cater to multi-generational travel – is the main drag. The Somerset is a favorite for broods, thanks to its oversized villa-style accommodations (choices range from 1- to 5-bedrooms); complimentary kids club (offering a long list of engaging activities); and attentive staff, who are always at the ready to outfit little ones with a bicycle or help them catch a lizard. At the nearby Grace Bay Club, the VIK (Very Important Kids) program greets kiddos with their own welcome amenities, while the Kids Town—equipped with a clubhouse, playground, and treehouse—has free activities like field trips to a conch farm, snorkeling and paddleboarding, astronomy lessons and more. If you want to go all out on family fun, check in to the all-inclusive Beaches, where the younger set will love the Sesame Street experience (with costumed characters) and Kids Camp, where teens can hang out at the Xbox Lounge and DJ Scratch Academy, while adults can chill in peace around the pool or at the spa. There's even an on-site water park, complete with water cannons, lazy rivers, and a surf simulator.

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