Which Caribbean Island Is Right for You?

Ideal For: Beach Bums, Divers, Families, Food Snobs, Golfers, Value

Most travelers flock to the Caymans for two things: diving at sites like Stingray City (where you can swim with stingrays, natch) and Seven Mile Beach, Grand Cayman’s marquee stretch of pristine sand. Resorts there, like the 365-room Ritz-Carlton, Grand Cayman, are mainstays for many reasons—the Greg Norman-designed golf course, Eric Ripert seafood restaurant, and La Prairie spa among them—but with this may come crowds.

For a more off-the-beaten-path experience, head to Le Soleil d’Or, a new retreat on 12-mile-long Cayman Brac, with a beach club, a 20-acre organic farm, and private villas. No matter where you stay, don’t miss Grand Cayman’s Camana Bay. The 600-acre waterfront development features retail spaces, landscaped boulevards, and an observation tower with 360-degree views of Seven Mile Beach, George Town, and the North Sound.

Ideal For: Beach Bums, Couples, Families, Food Snobs

Even with its winter holiday crowds and hefty price tags, the beauty, charm, and Gallic flair of St. Bart’s is undeniable. On Flamands Bay you’ll find the rebranded Cheval Blanc St.-Barth Isle de France, which has all the amenities you’d expect from its owner, luxury-brand conglomerate LVMH: 40 crisp, all-white rooms, a fitness center overlooking the sea, and the Caribbean’s only Guerlain-branded spa (book the Abeille Royale lifting and firming facial).

At the other end of the island, Le Guanahani recently unveiled a four-year, $40 million renovation that transformed its 67 guest cottages into chic enclaves with pops of turquoise, yellow, and lavender, plus beach-meets-safari design flourishes, like framed maps and custom furniture by Luis Pons. The hotel also offers two beaches, both clay and grass tennis courts, stand-up paddle board and aqua fitness classes, plus a Frédéric Fekkai hair salon and Clarins spa.

If you can step away from the hotel, try one of the island’s many French-inspired restaurants—La Gloriette for crisp salt-cod fritters; Le Grain de Sel for crab-and-lentil salad; L’Esprit Saline for a menu of Provençal-style dishes that changes daily. However, the ultimate culinary experience is undoubtedly found at one of Chef Jean-Georges Vongerichten’s two restaurants at the legendary Eden Rock – St. Barths.

Ideal For: Couples, Families, Sailors

Sailing is one of the biggest draws for travelers to this archipelago of 60 islands, cays, and islets. Companies like Festiva Sailing Vacations operate six- or eight-person catamarans whose captain and first mate will chart your course—exploring places like the Baths on Virgin Gorda, Sage Mountain National Park on Tortola, and Loblolly Bay Beach on Anegada.

For those who prefer to remain on dry land, Virgin Gorda’s Rosewood Little Dix Bay recently converted its 10 iconic, elevated tree-house cottages into five large suites with wraparound terraces. The resort, founded by Laurance D. Rockefeller in 1964, can arrange bespoke services like private beach picnics, en-suite rum tastings, and scuba diving instruction at it’s own on-site watersports center.

Also noteworthy are Oil Nut Bay, a 300-acre estate with eight stylish houses, ideal for multigenerational families, and Guana Island, a private-island resort with 18 airy stone cottages and villas.

Ideal For: Beach Bums, Couples, Families, Food Snobs, Golfers, Value

Situated slightly East of the Atlantic hurricane belt, Barbados is a safe bet for travelers year-round, though the island does experience both wet and dry seasons (mid-December through April is ideal with the least amount of rainfall, but that’s also high season).

At places like the iconic Sandy Lane resort, golfers can put their game to the test at three different courses (the hotel was the setting for Tiger Woods’s 2004 wedding), while the Coral Reef Club hosts a spa designed by Neil Howard, who also helmed wellness concepts at the Armani hotels in Dubai and Milan.

In general, the island is a melting pot of English, African, and West Indian heritage—a dynamism that comes through in a friendly local population and strikingly rich cuisine. Don’t miss the lunchtime wood-fired pizzas and the sea bass Provençal entrée at the Lone Star Resort’s popular on-site restaurant.

Ideal For: Couples, Families, Value

Flying into Nassau, it’s impossible to miss the salmon-colored mega-resort that is Atlantis Paradise Island—a luxury hotel and casino with a celebrity following. But new competition is entering the fold as the $3.5 billion Baha Mar opens this summer. The waterfront development will include a Jack Nicklaus-designed golf course, world-class gambling facilities, more than 40 restaurants, and four hotels.

If big resorts aren’t your thing, make for Eleuthera, a 110-mile-long island just 20 minutes away by plane. There you’ll find The Cove (pictured), a recent T+L It List winner, which hosts 60 rooms on a private, 40-acre property with two beaches and a picturesque bluff—the ideal spot for sunset cocktails.

Arguably more picturesque is Harbour Island, or “Briland” as locals call it, a three-and-a-half-mile-long pink-sand cay just off Eleuthera. (If you’re coming from Nassau, fly into North Eleuthera Airport; from there, it’s a 5-minute ride by water taxi.) Briland may be small, but it has luxury havens like Pink Sands Resort, Coral Sands, the Dunmore, and the Ocean View Club, not to mention fantastic restaurants (the Landing, the Rock House) and stylish local boutiques (India Hicks, Shine, Blue Rooster).

Ideal For: Beach Bums, Couples, Families

Comprised of two island groups (the Turks, smaller; the Caicos, larger), located southeast of the Bahamas, Turks and Caicos had virtually no tourism twenty years ago. Today, more than 200,000 travelers visit the archipelago every year—and the hotel landscape has grown in step.

On Providenciales, the most populous island, there are a number of all-suite resorts set on Grace Bay Beach—one of the territory’s finest—like the family-friendly Regent Palms, the grande dame Grace Bay Club, and the über-luxe Amanyara.

For those looking further afield, Parrot Cay by COMO is a thousand-acre private-island resort 35 minutes from Providenciales by water taxi. Guests can partake in Ayurvedic massages, open-air beach yoga, and traditional Javanese bath rituals through the resort’s award-winning COMO Shambhala Spa.

Ideal For: Adventure-seekers, Beach Bums, Couples, Divers

Honeymooners flock to sought-after resorts like Jade Mountain and Ladera, which have open-air guest rooms with private plunge pools overlooking the Caribbean Sea and the Piton Mountains. The island is actually one of the most mountainous in the region, home to a rainforest, waterfall trails, botanical gardens, and Sulfur Springs in the capital city of Soufrière, where travelers can take mud baths.

Also not to be missed are Sugar Beach—location for the recently opened Sugar Beach, A Viceroy Resort—and dolphin and whale-watching cruises out of Marigot Bay, home to the new Capella Marigot Bay.

Ideal For: Beach Bums, Couples, Families, Golfers, Value

The eastern half of the island of Hispaniola (the western part is Haiti) was once overlooked by the monied upper classes, which favored more popular Cuba and Puerto Rico. That changed in the 1970s with the opening of Casa de Campo, a 155-room historic landmark property that still lures luxury travelers today. Golfers especially find a haven in the 7,000-acre resort’s three courses from award-winning designer Pete Dye.

A challenging game is likewise presented at the Jack Nicklaus-designed course at Eden Roc at Cap Cana. With its white Côte d’Azur-style buildings and Mediterranean restaurant, the resort could easily be mistaken for one on the French Riviera. Look closer, however, and you’ll see it’s pure Caribbean: powdery white sand, lush jungle, and 34 villas and suites done in tropical shades with private plunge pools.

On the island’s eastern shore, Punta Cana has become dotted with all-inclusive resorts, but chic enclaves do exist. Legendary fashion designer Oscar de la Renta imagined the plantation-style interiors at Tortuga Bay, Puntacana Resort & Club, a hotel that also features an expansive nature reserve with 12 freshwater lagoons.

Beach purists should seek Puerto Plata, an area on the less-frequented northern shore that’s remained largely under the radar—until now, with the city-glamour-infused Gansevoort Playa Imbert, in soft opening until June 2015, and the forthcoming Aman Villas (slated for completion by year’s end).

Ideal For: Beach Bums, Couples, Food Snobs, Golfers

If you’re looking for top-notch hotels and pristine beaches, look no further than Anguilla. Unlike its volcanic neighbors, Anguilla’s flat, limestone landscape gives way to incredible beaches: Shoal Bay, Meads Bay, Junks Hole, and more. The island’s crown-jewel resort, the 20-acre Malliouhana, An Auberge Resort, reopened late last year following a three-year closure for renovations.

Nearby Cap Juluca also got a recent face-lift; expect Moorish-inspired architecture and Maundays Bay’s startlingly blue waters, which guests can ply in the resort’s new yacht, Juluca Pride. Golfers will want to settle in at CuisinArt Golf Resort & Spa, home to Anguilla’s first and only 18-hole course (designed by Greg Norman), as well as a state-of-the-art hydroponic farm and five on-site restaurants.

The island has plenty of inventive off-campus dining options, like Hibernia Restaurant, which offers a menu of Asian-Caribbean fusion, and B&D’s BBQ, a casual roadside tent in Long Bay renowned for its ribs and roast chicken.

Ideal For: Adventure-seekers, Couples, Divers

Straddling the dividing line between the Windward and Leeward islands, Dominica is often called “the nature island,” thanks to its volcanic landscapes, lush rainforests, boiling hot springs, extensive hiking trails, and pristine coral reefs. It’s largely been a secret refuge for sunseekers and soul-searchers—but is now stepping into the limelight, thanks to a new world-class resort.

Situated on top of a dramatic cliff overlooking the Caribbean Sea, Secret Bay is a luxe eco-retreat comprised of one- and two-bedroom villas with a distinctly Caribbean feel—bi-folding doors allow open-air living, and furnishings are made of Dominican red cedar by local craftsmen. The resort is bordered by the Cario River and surrounded by two white-sand beaches on Prince Rupert Bay. But don’t expect to sit on the beach—activities include scuba diving, whale watching, hiking a UNESCO World Heritage-designated national park, boat rides through river mangroves, and more.

Ideal For: Beach Bums, Couples, Families, Food Snobs, Value

This easy-to-get-to destination (read: no passport required for entry) is back on the map with a surge of recent investment in places like San Juan, Dorado Beach, and the nearby island of Vieques. The 319-room Condado Vanderbilt Hotel made a splashy $200-million opening in the capital late last year. The 1919 Spanish Revival landmark—which hosted such names as President Roosevelt, Charles Lindbergh, and Bob Hope—had been closed for more than a decade.

Forty minutes away lies Dorado Beach, a Ritz-Carlton Reserve. The private estate resort, originally founded by Laurance D. Rockefeller, saw its reinvention in late 2012, courtesy of renowned architect Bill Bensley.

On the small satellite island of Vieques, the new El Blok is shaking things up with bold design and cuisine from Puerto Rican top chef José Enrique, whose namesake restaurant in the Santurce neighborhood of San Juan still draws lively crowds with his contemporary-tropical menu.

Ideal For: Couples, Families, Value

With nearly 1.5 million annual visitors, Aruba gets a bad rap for being overly touristy—the island, located 15 miles north of Venezuela, is less than 20 miles long, after all. But this reputation doesn’t take into account its diverse landscapes and experiences.

Sure, there are casino-resorts aplenty, but sophisticated versions exist, like the Ritz-Carlton, Aruba, located on the northernmost (quieter) end of Palm Beach. The hotel features two pools, five restaurants, and a 15-treatment-room spa (try the Dushi Tera salt scrub). Further south lies the Hyatt Regency Resort Spa and Casino, another upscale option with an 8,000-square-foot, three-tiered pool and 10 restaurants and bars, as well as Bucuti & Tara Beach Resorts, a sustainable, adults-only boutique hotel with European charm.

For an excursion outside the resort hotbed, head to Arikok National Park or Baby Beach, where you can fill up on johnnycakes at local favorite Big Mama Grill. Travelers can also book a half-day excursion with De Palm Tours (the company is partnered with a number of resorts) to see inland sights, like the California Lighthouse and the Casibari Rock Formation.

Ideal For: Beach Bums, Couples, Food Snobs

It’s safe to say Jamaica is in the midst of a renaissance. A handful of stylish, iconoclastic resorts are debunking the island’s reputation as a couples-only destination. Rather than sequestering guests behind closed gates, these new hotels are tapping into the island’s complex topography, rich history, and vivid culture.

Hotelier Chris Blackwell (also the founder of Island Records) transformed GoldenEye—the north-shore estate where James Bond creator Ian Fleming lived and wrote—into an Island Outpost hotel a few years back. Guests stay in rustic but stylish seaside bungalows designed by Barbara Hulanicki, founder of London’s legendary fashion store Biba.

In the Port Antonio area—a playground for Hollywood stars in the 1950s and ‘60s—the newly restored Trident Hotel has 13 waterfront villas, overseen by British music-industry vets John Baker and Steve Beaver. They also manage a sister property, the Geejam, set on a six-acre estate near Frenchman’s Cove with an on-site professional recording studio. Travelers can also now expect locally sourced cuisine at grande dames like Jamaica Inn, in Ocho Rios, and Montego Bay’s Round Hill Hotel and Villas (try the Jamaican rock shrimp and pole beans with fresh mint from the resort’s own organic garden).

Ideal For: Beach Bums, Divers, Families, Value

St. John, St. Thomas, and St. Croix are the main draws for travelers to western half of the Virgin Islands archipelago—and the fact that a passport isn’t required for entry. On St. John, the 170-acre Caneel Bay Resort is a stalwart originally founded by Laurance D. Rockefeller, which emphasizes green living (no television or phones).

Two-thirds of the island has been declared a national park, making it a popular destination for snorkeling, hiking, and horseback riding. Green and hawksbill sea turtles are known to nest on St. Croix’s pristine white-sand beaches in places like Sandy Point and Jack and Isaacs Bay.

Meanwhile, on St. Thomas, the Marriott Frenchman’s Reef Resort underwent a $45-million renovation in 2011, with interiors designed by Hirsch Bedner Associates, which also oversaw a makeover at the Beverly Hills Hotel.