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What’s the Best Caribbean Island for You?

Whether you’re a beach bum, a diver, a foodie, or a golfer—there’s a Caribbean island just for you.

Àni Villas Dominican Republic Photo: Courtesy Àni Villas Dominican Republic

Of course, we all know the Caribbean is the perfect place for sun, sea, and sand. But not all islands were created equal: This dreamy cluster of isles stretching more than 2,000 miles across the Caribbean Sea is home to a wealth of destinations, each with its own unique topography, attractions, and individual style.

Some islands were made for adventurers—with snorkeling, hiking, diving, and more—while other are perfectly suited for beach bums, featuring idyllic sands and picturesque palm trees. Then there are the islands that are ideal for foodies, offering access to some of the world’s top chefs. So how do you choose where to go?

Our handy guide breaks down 15 of the most alluring islands—and who will love them most. Whether you’re seeking wellness, seclusion, activity, or just a really beautiful beach, we’ve got you covered for your next Caribbean vacation (and every one after that).

St. Lucia

Best for: Romantics

Most recognizable by its Pitons—two massive volcanic spires set against the beautiful Caribbean Sea—St. Lucia is a favorite for honeymooners and nature lovers. No wonder: It’s one of the islands’ lushest destinations, with waterfalls, rainforests, botanical gardens, and hot springs. The place to stay is the award-winning Jade Mountain, where the “sanctuaries” (as the guest room are called) are architectural wonders, open to the elements with infinity-edge pools stretching out to the horizon—and the Pitons. The resort’s rooftop Jade Mountain Club claims the best sunsets—and rum punches—on the island. For a livelier atmosphere, check into Sugar Beach, a Viceroy Resort, which, set on a powdery-white stretch of sand smack in between the two Pitons, offers 118 cottages, villas, bungalows, and residences.

Jade Mountain

Jade Mountain  Photo: Courtesy Jade Mountain


Turks & Caicos

Best for: Wellness Seekers

Yogis and devotees of Ayurvedic medicine have been making pilgrimages to the Turks & Caicos islands since 1988, when Como Parrot Cay opened on an ultra-exclusive private island just off the mainland of Providenciales. There, celebrities, high-rollers, and Eat, Pray, Love wannabes can mellow out, firm up, and wind down. Rent out Donna Karan’s on-property Balinese-inspired sanctuary—complete with its own yoga studio—when the fashion designer isn’t in residence, or stay in one of Como’s breezy beachfront villas. For a mainland wellness escape, head next to cult-favorite Amanyara, where the extensive spa offerings include everything from detox retreats to fitness programs.

Como Parrot Cay

Como Parrot Cay  Photo: Courtesy Como Parrot Cay

Ambergris Caye, Belize

Best for: Avid divers

Belize’s largest island is a must-visit destination for serious scuba divers angling to explore the Belize Barrier Reef, the largest of its kind in the Northern and Western Hemispheres. The island’s main town of San Pedro is home to most of the resorts, but divers in search of a more secluded experience should head just three miles off the mainland to Cayo Espanto, a private-island resort where the white sands and clear waters are exclusive to a handful of lucky guests. When you’re not busy swimming with colorful triggerfish and parrotfish, you’ll be soaking up the sun at your private plunge pool.

Cayo Espanto

Cayo Espanto  Photo: Courtesy Cayo Espanto Private Island Resort


Best for: Foodies

The Caribbean hasn’t quite gained a reputation as a culinary mecca, but there’s one destination that’s giving foodies a reason to go island-hopping: Baha Mar has made Nassau a gastronomic hot spot with its roster of celebrity-chef restaurants, including outposts of Danny Elmaleh’s Cleo and master sushi chef Katsuya Uechi’s Katsuya. More mouthwatering cuisine can be found at the nearby Atlantis the Cove, which is home to restaurants by Nobu and José Andrés.

SLS Baha Mar

SLS Baha Mar  Photo: Courtesy SLS Baha Mar


Best for: Beach Bums

Formed by coral and limestone, Anguilla is flat and long—the perfect conditions for an island filled end to end with powder-white beaches. And there’s no shortage of luxurious ways to lay about on the picture-perfect sand. Stay at the stylish Four Seasons Resort & Residences Anguilla, where Kelly Wearstler–designed interiors (think organic natural woods mixed with sleek marble and glamorous details) and top-notch service provide an idyllic setting for a whole lot of bumming around. Or claim a more private stretch of beach by staying at Ani Villas Anguilla, a pair of exclusive-use mansions overlooking isolated Little Bay Beach. And come winter 2018, the island will welcome with wide arms the post-hurricane reopening of two longtime island favorites: Malliouhana, an Auberge Resort, occupying 25 acres along Meads Bay, and the Moorish-style Cap Juluca, which will relaunch as a Belmond property in November.

RELATED: 12 Hotels to Escape to in the Caribbean Right Now

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla  Photo: Courtesy Four Seasons Resort and Residences Anguilla


Best for: Royals

Mustique may have been Princess Margaret’s playground, but she was far from the only royal who made it her escape from societal pressures. Prince William and Duchess Kate Middleton have been known to vacation on the island—and so have rock royalty Mick Jagger and David Bowie. Of course, mere mortals are invited to the powdery shores of this St. Vincent and Grenadines island—provided they can get a reservation at the Cotton House Hotel, an exclusive little getaway that was recently re-envisioned by legendary designer Tristan Auer. For the traveler with a royal obsession, however, there’s only one place that will do: Les Jolies Eaux, which can be rented for roughly $30,000 per week, is the former vacation home of her royal highness herself, Princess Margaret.

Cotton House

Cotton House  Photo: Courtesy Cotton House


Best for: Billionaires

If Mustique is known for its millionaires, then this little island in St. Vincent & the Grenadines is known for its billionaires. Measuring just 5 square miles, the Edenic isle of Canouan has welcomed more than its fair share of VVIPs, from Bill Gates to Tom Cruise. And like Mustique, there’s only one hotel for the jet-setters who don’t already have a home there: The ultra-expensive Pink Sands Club, a Mandarin Oriental resort that comprises 26 over-the-top suites and villas. Next door, the Canon Estates offers more exclusivity with its impressive collection of rental estates. And on the southern end of the island, a new 120-slip marina is making the island the Caribbean’s next big super-yachting destination.

Pink Sands Club

Pink Sands Club  Photo: Courtesy Pink Sands Club

St. Barts

Best for: Luxury Seekers

Of course, the French know luxury. Add to that one of the Caribbean’s most beautiful and exclusive islands, and you’ve got a destination that truly speaks to the jet set. Most guests arrive by private plane or superyacht—and they expect nothing but the best when they get there. That means top-tier resorts like Le Guanahani, Eden Rock – Saint Barths, and Cheval Blanc—all of which are soon to reveal stunning new renovations following 2017’s Hurricane Irma. In the  meantime, properties like Villa Marie Saint-Barth, restaurants like Shellona Beach, and exclusive-use residences like the $400,000-per-night Camp David are happily catering to the discerning clientele.

Villa Marie Saint-Barth

Villa Marie Saint-Barth  Photo: Courtesy Villa Marie St. Barth

British Virgin Islands

Best for: Island Hoppers

There are only a few Caribbean destinations where you can hop from island to island like you’re in the Maldives—and the British Virgin Islands is the best of them. The standard-bearer, of course, is Sir Richard Branson’s Necker Island, the legendary private-island resort that has hosted everyone from Barack Obama to Kate Winslet (who famously saved Branson’s mother from a fire at the resort in 2014). Though the resort sustained serious damage during the Caribbean hurricanes of 2017, Branson has been tirelessly working to relaunch the iconic A-list getaway in late 2018.

Until then, the best bet for island-hopping travelers is Oil Nut Bay, a 400-acre retreat on Virgin Gorda. Make the resort—which features 88 over-the-top estates, an 8,700-square-foot beach club, a wellness center, and three Cliff House villas—your home base, and charter a yacht to bounce from star-studded isle to isle (Johnny Depp, Oprah Winfrey, Mick Jagger, and Keith Richards all reportedly own private isles in the British island territory). For a true castaway fantasy, drop anchor at one of the many uninhabited islands for a private picnic on a white-sand beach.

Necker Island

Necker Island  Photo: Courtesy Necker Island


Best for: Prepsters and Golfers

Barbados’s British colonial past lends a distinctly preppy vibe that still draws polo players and “it” Brits to its shores. (Prince Harry met the island’s unofficial royal, Rihanna, there in 2016.) For prepsters who like to hit the green, there’s no better place to stay than Sandy Lane, a member of Leading Hotels of the World with a famously challenging golf course—reportedly the most expensive ever built—by Tom Fazio. Even more Waspy is the resort’s décor, a mix of upscale colonial and over-the-top luxury. Don’t miss the Bajan Blue restaurant with its famous pink umbrellas lining the turquoise sea.

Barbados aerial view

Aerial view  Photo: Milan Portfolio/Shutterstock


Best for: Nature Lovers

Virtually untouched by tourism until the 1980s, Dominica is a wild one among the Caribbean’s typically manicured islands. Roughly half the island is covered in rain forest, and one-third is national parkland. Natural wonders abound, from volcanoes, deep gorges, and rivers to waterfalls, hot springs, and tropical gardens like Papillote, which boasts 81 varieties of orchids. True to the island’s untouched appeal, resorts are few and far between. The best is Secret Bay, an eco-friendly paradise perched on a promontory above Tibay Beach. There, just eight secluded bungalows and villas are nestled into the native jungle like luxurious treehouses. Don’t miss out on the resort’s myriad adventures, including night snorkeling, jungle biking, and stand-up paddleboarding.

Secret Bay Dominica

Secret Bay  Photo: Courtesy Secret Bay


Best for: Laidback Luxury-Seekers

Bob Marley’s birthplace is legendary for its Rastafari culture and laid-back lifestyle. But that’s far from all the island has to offer: Beautiful landscapes, excellent snorkeling and diving, and delicious Creole cuisine are just a few of the draws that keep tourists coming year after year. To experience the best the island has to offer—and avoid the tourist traps—bypass popular destinations like Ocho Rios and Negril, and head instead to Oracabessa for a stay at Goldeneye resort. Owned by Rock and Roll Hall of Famer Chris Blackwell—founder of Island Records and the man who discovered Bob Marley—the resort is a private oasis that captures the best of Jamaica, from beautiful beaches and tranquil lagoons to expansive farmlands and top-notch local cuisine. The villas have a touch of kitsch with details like colorful Smeg mini-fridges and vibrantly patterned daybeds, while the Bizot Bar is the island’s coolest place for a drink, showcasing vintage Island Records albums and playing recordings of Paris’s famous Radio Nova radio station. Pair Goldeneye with an exploration of the island’s Blue Mountains—where Jamaica’s revered coffee beans are grown—by staying at Blackwell’s other resort, Strawberry Hill.

The Tryall Club

The Tryall Club  Photo: Courtesy The Tryall Club

Puerto Rico

Best for: History Buffs

A quick and easy getaway for American citizens, Puerto Rico is rich in history, Latin culture, and legends of pirates. History buffs will love exploring San Juan’s old forts Castillo San Felipe del Moro and Castillo de San Cristóbal, which date back to the 16th century. Stay in the midst of it all by check in to Hotel El Convento, a five-star hotel set within a former convent and the best base for wandering San Juan’s cobblestone streets lined with colorful colonial buildings and relaxing on the beaches. Or explore the coastline while staying close to the city—which is still recovering from the Caribbean hurricanes of 2017—with a stay at the beachfront Ritz-Carlton, San Juan (set to reopen later this year).

There’s plenty for history buffs outside of the city as well: Laurence S. Rockefeller first opened the iconic Dorado Beach, some 30 miles west of San Juan, in 1958. Today, the Ritz-Carlton-managed resort—which is currently undergoing repairs due to Hurricane Maria—is a magical re-invention of the legendary oasis.

Hotel El Convento

Hotel El Convento  Photo: Courtesy Hotel El Convento


Best for: Culture Vultures

Isolated for decades, the isle of Castro and classic cars is the forbidden fruit of Caribbean. Though legislation has waffled in the last few years, it remains possible for travelers to visit on an educational visa—and what an education indeed. Any exploration of the island of Cuba will start in Havana, where travelers will discover everything from the local cuisine at paladares to the regional art (a part of culture long nurtured by the Cuban government). For the most immersive experience—and to bypass much of the bureaucratic red tape associated with a visit—make sure to book your trip through a respected local outfitter like Cuba Educational Travel. With an expert’s help, travelers can expect to stay in Cuba’s best accommodations, like the Gran Hotel Manzana Kempinski La Habana, set within a historic building in central Havana, and organize exclusive experiences throughout the country, including at its untouched beaches.

Gran Hotel Manzana Kempinski La Habana

Gran Hotel Manzana Kempinski La Habana  Photo: Courtesy Gran Hotel Manzana Kempinski La Habana

Dominican Republic

Best for: Design Gurus

The Dominican Republic’s most famous native, designer Oscar de la Renta, once said, “I like light, color, luminosity. I like things full of color and vibrant.” It’s no surprise that the native of this verdant tropical island would revere brightness and color—the Dominican Republic is one of the Caribbean’s most vibrant destinations. And it’s also one of its most stylish thanks to de la Renta, who designed elements of two of the island’s most iconic resorts: Casa de Campo Resort & Villas and Tortuga Bay. At the former, the fashion designer’s lavish estate is available for rent, while at the latter, a collection of 13 villas were created by the master himself. After walking in the couture legend’s footsteps, design aficionados can head to the north of the island to visit two more stylish hotels: the sleek Amanera—a Balinese-inspired retreat on the shores of Hispanola—and the chic Playa Grande Beach Club, with white-washed bungalows and a vintage details.

Tortuga Bay Puntacana Resort & Club

Tortuga Bay Puntacana Resort & Club  Photo: Courtesy Tortuga Bay Puntacana Resort & Club

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