With dozens of countries and thousands of islands, picking your destination can be a bit overwhelming. Use this guide to help you find the island that’s your perfect match.
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Perfect for: Dining and Drinking
There are a lot of great dining destinations in the Caribbean, but only one with its own Zagat guide: Barbados. Drawing on the island’s mix of sophisticated culture and great local culinary traditions, upscale Bajan restaurants serve up everything from West Indian fusion cuisine to elegant Italian and Asian dining. When you want to go local—really local—drop in at one of the island’s thousands of rum shops, where you can snack on West Indian favorites like Pudding and Souse and Bajan Pepper Pot, or simply enjoy a nice “lime” with friends over a few drams of local rum from distillers Mount Gay, Cockspur, and Doorly’s.
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Photo: Courtesy The Crane Resort, Barbados
Barbados restaurants like The Cliff, The Tides, and Champers are consistent favorites of discerning Bajans and visitors alike for a memorable fine-dining experience. For classic Italian, the go-to is Daphne’s in St. James; Zen at the legendary Crane Resort serves the best Thai and Japanese cuisine. Spice things up with West Indian cuisine at the uber-casual Roti Den on Payne’s Beach, or embrace the island spirit at the Friday night Oistins Fish Fry—part seafood festival, part street party. Rum shops can be found almost anywhere on the island, but St. Lawrence Gap is nightlife central on Barbados: in addition to rum shops like the Watering Hole and Cool Castaways you’ll find a lively street scene and restaurants serving food and playing music from all over the world.
Perfect for: Diving
You don’t have to look far for a great dive spot when you’re visiting Bonaire: the entire island is surrounded by the Bonaire National Marine Park, a sanctuary established in 1979 that has helped keep Bonaire’s fringing reef one of the healthiest in the world. Teeming with life, Bonaire’s coral reefs are protected down to depths of 200 feet and are home to 57 species of coral and at least 350 fish species. SCUBA divers and snorkelers can enjoy more than 86 dive sites around the islands of Bonaire and Klein Bonaire, including the famous 1,000 Steps and Buddy’s Reef.
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Photo: Courtesy Divi Resorts
Legendary dive resorts like Captain Don’s Habitat and the Buddy Dive Resort will expertly guide your underwater adventure on Bonaire: each offers packages that include accommodations, dining, and multiple dive trips. When you want to be next to the water instead of underwater, daytrippers to Klein Bonaire will find the best beaches; Washington-Slagbaai National Park, which covers about one-fifth of the island of Bonaire, is a habitat and nesting ground for local wildlife and birds with undeveloped beaches and hiking trails. Fuel your explorations with a stop at the Maiky Snack for local goat soup and the polenta-like funchi, the national dishes. The Divi Flamingo Beach Resort is an all-inclusive that comes alive at night thanks to having the island’s only casino.
Perfect for: Romance
St. Lucia’s pointy Pitons—twin volcanic peaks thrust upward more than 2,000 feet above the sea—create arguably the most dramatic and lovely landscape in the Caribbean. The Pitons serve as the backdrop for countless wedding photos as well as the view from St. Lucia’s unparalleled collection of romantic upscale resorts (many of which are couples only). Great beaches, attractions ranging from zip lining and rainforest hiking to visiting the island’s famous “drive-through” volcano, and nightlife and dining in Rodney Bay and Castries (plus the weekly “jump up” street party in Vieux Fort) make St. Lucia ideal for honeymooners and all couples with a yen for local culture and light adventure.
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Photo: Courtesy Sugar Beach, a Viceroy Resort
The all-inclusive Rendezvous and BodyHoliday resorts have a couple of the best spas in the Caribbean, while Coconut Bay offers the flexibility of getting in touch with your inner kid at the Splash waterpark and with a game of paintball or chilling on the adults-only Oasis section of the resort. The Viceroy Sugar Beach feels more South Pacific than Eastern Caribbean, set at the base of a palm-covered slope on a quiet cove between the Pitons. We love the whitewashed villas of Cap Maison, where you’ll dine at two of the island’s best restaurants, including the laid-back Naked Fisherman and the elegant, open-air Cliff with its unparalleled sunset views of the Caribbean, Pigeon Island, and Martinique. The hillside, three-walled villas at Anse Chastanet are among the most beautiful places to lay your head in the Caribbean.
Photo: Danita Delimont/Getty Images
Perfect for: Dancing
From reggae to soca, calypso to zouk, Caribbean music is famous around the world. In Puerto Rico, locals and visitors sway to a Latin beat ’til the wee hours of the morning in the Caribbean’s de facto capital city, San Juan, and beyond. Trendy dance clubs pound out reggaeton and Latin-influenced hip-hop and house music, but there’s also plenty of opportunities to enjoy salsa and merengue. Bomba, a style of folk music dating back to the 17th century, can be heard (and danced to) at local festivals. Locals ages 9 to 90 not only will be happy to take a turn on the dance floor with you, but also will show you how to move your body to a Latin beat if you’re a rookie.
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Photo: Courtesy Hotel El Convento
In Old San Juan, the Nuyorican Cafe is a combination bar and theater with live salsa music, while in the tourist district of Condado a younger crowd flocks to the terrace at the di Zucchero restaurant (Club Brava at the La Concha resort in Isla Verde is another option for dancing to house, hip-hop, and Top 40). Triana Tapas & Flamenco, a Spanish restaurant in Old San Juan, is among several places in town where you can get free salsa lessons (Tuesday and Wednesday nights). Condado and Isla Verde are the big beachfront resort districts within easy reach of Old San Juan, but if you want to stay in the old walled city itself, check out El Convento, a boutique hotel in a historic former convent.
Perfect for: Family Fun
Aruba has grown into one of the most popular destinations in the Caribbean without sacrificing its reputation as “One Happy Island”: people here are just plain nice, and you’ll be greeted and treated warmly whether you’re immersed in one of the island’s beachfront tourist areas or exploring Aruba’s rugged backcountry. The welcoming attitude makes Aruba a great place to bring the kids, only the most jaded of whom will be bored on an island where activities range from the usual array of resort-area water sports (diving, jet-skis, parasailing, etc.) to submarine tours and explorations of Aruba’s desert landscape by horseback, Jeep, or ATV.
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Atlantis Submarines offers a memorable underwater adventure, diving 130 feet down to view fish, coral reefs, and hulking wrecks. Kids of all ages will love a swashbuckling snorkeling tour with the Jolly Pirates, highlighted by a plunge off the pirate ship’s rope swing. For outback adventures by horse or ATV, we love Rancho Notorious; the all-inclusive DePalm Island has beaches, waterslides, snorkeling, unlimited banana-boat rides, and more. Several of the island’s big-name hotels have excellent family-friendly amenities, like the Hyatt Regency Aruba Resort and Casino with its multilevel pool and waterslides and the Marriott Aruba Surf Club, which has a lazy river pool surrounded by lush landscaping. Palm Beach is tops with families thanks to its endless array of watersports activities and its proximity to the movies, fast food, live music and nightly dancing water show at the Paseo Herencia shopping area.
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Perfect for: Sailing
If sailing around a group of idyllic tropical islands for a few days—taking a break from sunbathing on deck only to stop at pristine beaches, hidden dive spots and friendly beach bars—sounds like your idea of paradise, set course for the British Virgin Islands. With 15 inhabited islands and dozens of smaller islets centered on Sir Francis Drake Channel, the BVI is a sailor’s paradise, whether you’re a couple bare-backing a catamaran or a group of friends chartering a crewed luxury yacht. Fair winds and calm seas will carry you to beach bars where you can wade ashore for rum drinks and local lobster, and when it’s time for the inevitable afternoon nap you’ll find countless secluded coves and beaches where you can relax and recharge.
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Photo: Courtesy Guana Island
You can dive among the dramatic underwater boulders at The Baths on Virgin Gorda or go deep to explore the wreck of the RMS Rhone, a 19th-century mail ship. Popular ports of calls for lunch and libations include the Soggy Dollar, birthplace of the Painkiller punch, and Foxy’s on Jost Van Dyke, which has its own microbrewery. Time for a midday nap? You’ll find lonely, lovely strands at White Bay Beach on Guana Island or pretty much anywhere on flat, distant Anegada. Day or night, naughty fun is right in the wheelhouse of the famously libertine Willy T, a floating boat bar off the coast of Norman Island.
Perfect for: Getting Active
Sure, you can spend your days lounging poolside at one of Jamaica’s countless all-inclusive beach resorts. But doesn’t diving off a cliff, rafting or tubing a tropical river, or riding horseback through the surf sound like so much more fun? Jamaica is a big, big island, with vast terrain to explore beyond the typical tourist areas, from biking the cool Blue Mountains to hiking the twisting roads through rugged Cockpit Country. Former plantations have been converted into adventure-sports centers complete with zip lining and ATV tours. Paintball, water parks, laser tag, cliff diving—you’ll find all this in Jamaica, as well. And yes, you can take a ride on a Jamaican bobsled!
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Negril’s rugged cliffs provide a (literal) jumping-off point for plunging into the Caribbean Sea at Rick’s Cafe, while that “bobsled” is actually a rollercoaster-style thrill ride at Mystic Mountain near Ocho Rios, which also has a canopy zip line course. Negril, Montego Bay and “Ochi” are the big tourist areas, and while some of the “adventures” you’ll see touted in these places are pretty tame (dolphin encounters, climbing Dunn’s River Falls), you can get out into the wilds quickly enough. Falmouth is very convenient for rafting on the nearby Martha Brae River and exploring Cockpit Country—good news for travelers calling at the cruise port downtown. The lovely Strawberry Hill resort is a great base if you want to venture into the Blue Mountains.
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Perfect for: Private Island Fans
St. Vincent and the Grenadines is a sparking chain of Caribbean islands where you can hop from private island to luxury private island on an indulgent yachting adventure. The main island of St. Vincent is where major scenes from the Pirates of the Caribbean were filmed; it’s a place of steep hills, wide valleys, quiet beaches and sparkling waterfalls, with Buccament Bay the mainland resort of choice. We spent the better part of a week on a chartered yacht out of the capital, Kingston, sailing from private island to private island like royalty; we could have done it for a month.
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Right off the coast of Kingstown, St. Vincent, is the charming Young Island—it’s so close you can ferry back and forth to the mainland for shopping or dining, but remains a lush little world of its own dotted with hillside guest villas. Palm Island is simply one of the most exquisitely lovely places you’ll ever see, while Petit St. Vincent invites you to settle into a private cottage and merely raise a flag when you need food, drinks, a massage, or other services. On Mustique, you can rub elbows with camera-shy celebrities at the Cotton House hotel or simply retreat to one of the island’s dozens of exclusive private villas.
Perfect for: Fishing
The warm, shallow waters of the Out Islands of the Bahamas—and the darker depths of the ocean trenches just beyond—are among the best fishing grounds in the Caribbean, if not the world. Ernest Hemingway, a passionate angler, helped put the Bahamas on the global map with novels like the The Old Man and the Sea and Islands in the Stream, and modern day sports fishermen (and women) can cast for everything from bonefish to blue marlin. Back ashore, you’ll find small, friendly island communities where the catch of the day will grace your dinner plate and tales of the one that got away can be shared over a few cold Kalik beers into the wee hours.
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Photo Courtesy of Bimini Big Game Club
You can do an Out Islands fishing vacation at whatever level of accommodation you like, from simple angler’s beach hut to a luxurious stay on a private island. The Andros Island Bonefish Club isn’t fancy, but the expert guides here will lead you to legendary fishing spots like the Land of the Giants in the flats surrounding the island. The Bimini Big Game Club Resort & Marina has been leading bonefishing trips since the 1940s and has grown into a full-service resort with a PADI dive center, while the Abaco Beach Resort offers guided eco-tours on land alongside fishing trips to the local shallows and deepwater pursuits of marlin and other game fish. Kamalame Cay is a private island off the coast of Andros that lures visitors with bonefishing by day and dining on fresh local seafood at night, including a popular surf-and-turf beach barbecue on Saturday nights. For the ultimate bonefishing experience, Deep Water Cay is a former private fishing club turned luxury escape. (read author Jonathan Miles's tale from Deep Water Cay, here.)
Photo: Jane Sweeney/Getty Images
Perfect for: History and Culture
The door to Cuba opens a little wider each year, and while you may not be able to travel to Florida’s near-neighbor entirely unfettered quite yet, the time is now to join a tour and experience Cuba’s rich history and vibrant culture before the arrival of mass tourism inevitably changes things forever. Founded in 1519, Havana is the heart of Cuba with a rumba beat: the ancient city’s treasures include its street musicians and Malecon lovers, theaters and cathedrals, art museums and cocktail lounges.
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You’ll still hear echoes of the Cold War at Havana’s Museum of the Revolution and Che Guevara’s mausoleum in Santa Clara, but you can also tour the tobacco fields of the Vinales Valley, explore the lovely Spanish colonial town of Trinidad, and lounge on the beaches of Varadero. With a few travel restrictions lingering, most Americans still travel to Cuba as part of a tour group, but the upside is that the best of these (like Insight Cuba) offer customized itineraries focused on interests like jazz, history, and baseball; some tours even include stays in a “casa particular,” or private home—the Cuban equivalent of a B&B. In Havana, a drink at La Floridita, a Hemingway favorite (and home of the original daiquiri), is a must; for dining, another of Papa’s old hangouts, the privately run “paladar” La Bodeguita del Medio, is one of the city’s more reliable spots for traditional Cuban food, and also claims to be the birthplace of the mojito.