Caribbean

Round Hill has long been a landing spot for starlets and artists: Grace Kelly, Alfred Hitchcock, Ian Fleming, Oscar Hammerstein, the list goes on. The Kennedys took their honeymoon here. But it’s Ralph Lauren (he bought a home here in the ‘80s, and describes the property as Eden) who’s left an indelible mark on the place: He designed the rooms. The resort leans more recreational than relaxed. Tennis is a fixture here, and if you time your visit right, you can attend clinic with a big-name player. A resort staffer will teach you to sail a Hobie Cat and leave you to whip over the waves. Water skiing? Glass-bottom boating? You’ve got it. And for little vacationers, there’s a nanny program and a kids club with a loaded calendar of activities, which changes daily.

On the volcanic island of Dominica—less touristy than nearby Antigua and St. Lucia, due to the fact that it’s harder to reach—Secret Bay is so private you might never run into other hotel guests. Very little of the property is shared space. Instead, visitors settle into one of the 25 villas on site, each perched on a rocky sea cliff or nestled into the jungle, with private plunge pools, open-air terraces, mattress and pillow menus, and views of the Carribean. You might never be called to leave your villa, except to explore the rainforest on horseback, spelunk through sea caves, or spend the night at the restaurant, Zing Zing. Although that too is optional: Every villa has a fully-equipped kitchen, and guests can request a private chef or spend evenings cooking for themselves. (More romantic when you aren’t responsible for groceries or the dishes, which are handled by the dedicated and thoughtful staff.)

Set on a private island in the Caribbean (it’s two miles off mainland Antigua and reachable only by boat) and enclosed in lush tropical foliage, Jumby Bay has 4.5 miles of powdery shoreline that are completely surrounded by crystal-blue coral-reef-sprinkled water. Every suite has a private plunge pool, and beautiful winding bike paths (the whole resort is brilliantly carless) take you right to the spa for sunrise yoga or breathwork or a treatment in a room with views of the ocean (you can actually hear the waves and breathe in the salt air). Get the facial (Tata Harper–designed, of course) with face-mapping therapy, exfoliation, massage, skin-reviving botanicals, and deep moisture.

The Jamaican mountains are the setting that inspired Ian Fleming to dream up James Bond—many of the books were written right here overlooking almond trees of the GoldenEye Villa. Despite the property’s storied past, it’s a casual, Caribbean-style luxury at GoldenEye: outdoor showers flanked by wide banana leaves, open-air architecture, and resolutely Jamaican cuisine—ackee, saltfish, plenty of bright fruit. The Fleming Villa is much as Fleming himself left it. Windows have no glass so you can catch the breeze; books are still heaped on the shelves; his writing desk invites you to come, sit, maybe bang out a few lines. The glassy water in the surrounding coves is made for kayaking, paddleboarding, glass-bottom-boating, snorkeling, swimming. The cottages and villas that frame the water’s edge—each sitting on their own acre—come with porches for private dining, claw-foot tubs, and gardens so green your eyes hurt.

During the day, L’Anse Guyac beach is a semicircle of tropical paradise: powder-fine white sand, crystal-clear azure water, a handful of palapas over navy-cushioned lounge chairs. But at night is when it really comes into its own. Torches light the narrow stone path down to the beach, where the sound of the water lapping is the perfect soundtrack for a predinner cocktail in the tented lounge on the sand. Try the L’Anse Guyac twist, created by local bartender Emmanuel May—fresh ginger, mint leaves, lime, and orange, with bitters, sugar syrup, Grenadine syrup, and Captain Bligh rum—it’s bright and not too sweet, with just a little kick. After drinks, move up to the open dining area. The highlight of chef Omar Bernardini’s menu is fresh seafood: There’s a jumbo crab appetizer with guacamole and locally grown mango; fresh-caught tuna tataki with sesame, wakame, and wasabi mayo; and a Catalan-style lobster with red onions, tomato, and mustard citronette. The standout is the Thai-inspired Rice Khao Sapparot, with prawns, pineapple, and yellow curry—the sweetness of the pineapple is the perfect complement to the heat of the curry.

The hospitality offered by “Scotchie’s” close-knit team of five—cook, butler, waiter, housekeeper, and gardener—is unmatched in Ocho Rios. Head chef Cherry consults with guests daily to craft seasonal menus that take into consideration dietary intolerances and food sensitivities. Rooms in this villa are impeccable, with high-quality linens and beautiful details, but the best feature of this five-bedroom house is its location. It’s right on the edge of a cliff, hovering above the White River Fish Sanctuary coral reef. Wake up early—sunrise over the Caribbean Sea from your bedroom window should help—and start the day with kayaking, paddleboarding, or snorkeling (all your gear is provided).

These spacious, coral-stone cottages are spread across tropical gardens on the west coast of Barbados. The air-conditioned rooms offer total privacy, and the larger villas—three- and four-person suites—are each equipped with a plunge pool, kitchen, and a lounge and dining area. The interiors feature traditional fretwork, rustic wood furnishings, comfortable beds, and cream-hued linens. The property has been run by the same family since the 1950s—the O’Haras—who know the ins and outs of their seaside villas well enough to intuit the needs of their frequently returning guests. Acting more as hosts than managers, they open their home to guests every Monday night for a cocktail party and outdoor BBQ buffet.

The first thing you’ll notice on this private island (accessible only by boat): white sand beaches as soft as talc and water so blue it looks like it’s been plugged in. Golf carts or bicycles bring you to one of the private villas that dot the circumference of the island, and accommodations run the gamut. There’s Mariposa, a nine-bedroom home, complete with personal tennis and basketball courts, and also more-modest one-bedroom suites, each with its own living room, private garden, plunge pool, and wraparound terrace. It’s impossible to make the wrong choice. Memorable touches include personalized stationery and a fleet of sailboats for guests (for both beginner and experienced sailors).

A blinding sea-blue view from the top of a cliff provides the ideal backdrop for an afternoon dipping in and out of infinity pools, lounging on day beds, and dining on delicious small plates. Everything at Sheer Rocks is prepared in-house, and the seafood is either line- or hand-caught. Quick bites include broccoli in ponzu yogurt and steak tartare, but if you have time, the seven-course tasting menu with wine pairings is worth it. Top off the day with a tropical dessert option: coconut-rum-soaked watermelon slices and pineapple tossed in passion fruit.

Even if you’re not a bird-watcher, the sight of one of the largest frigate bird populations—known for the balloon-like red jowl of its male species—is well worth the trip. Frigate is home to an estimated 100,000 birds that migrate between the Galapagos and the Caribbean, with the male population appearing from November to February, and the baby nestlings popping up from March to July. A boat ride through the mangroves of the lagoon brings you as close as five feet to the awe-inspiring creatures—since there are no predators on the island, they remain undisturbed by your presence. The population temporarily dispersed after 2017’s Hurricane Irma, but the birds have since returned, first slowly and now, happily, in droves.