Oracabessa Bay, Jamaica
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.
L’Ance Guyac Beach Club
L'Ance Guyac Bay, Canouan
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.
Scotch on the Rocks
Coconut Grove, Ocho Rios
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).
Coral Reef Club
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.
Jumby Bay Island
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).
Ffryes Beach, St. Mary
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.
Frigate Bird Sanctuary
Frigate Bird Sanctuary
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.
Carlisle Bay, St. Mary
This all-inclusive tennis retreat is designed to help you break a sweat with four championship tennis courts, a squash court, a basketball court, and a seventy-five-foot swimming pool, plus bocce and shuffleboard courts. There are even two beaches: one for water sports like Jet-Skiing, snorkeling, and scuba diving and another for lazing about. Active-minded visitors will be spoiled for choice, but if you want to take it slow, turn to the spa and wellness center for deep-tissue massages, yoga, and Pilates. Then retreat to your blue-and-white room, where you’ll find floor-to-ceiling glass doors, marble bathrooms—but no televisions, to ensure you’re taking advantage of the peace and quiet. We loved the attention to detail, like cold, scented towels poolside. At night, drop by Tamarind Tree for dinner and dancing and make a night of it—the fantastically fresh seafood is paired with wines from the property’s 25,000-bottle cellar.
Pigeon Point Beach, English Harbour
The (blissfully) underpopulated shores of Pigeon Beach have just a handful of bars and restaurants, including Catherine’s, an unassuming beach café preparing classical French cuisine with Provençal charm. Head chef Jack brings his years of experience in Michelin-starred restaurants to a seasonal menu featuring dishes such as lobster soup, fish carpaccio, stuffed calamari, and duck leg confit. The open dining area is accommodating enough for a walk-in off the beach, but since seats fill fast, it’s best to call ahead to reserve a table. You can make a day of it, too—between the allure of the Pigeon Beach’s crystal-clear waters, two cocktail menus (one dedicated entirely to gin and tonics), and nighttime entertainment from local jazz bands, Catherine’s is the best place to spend a lazy day.
Canouan’s a small island, and while there are plenty of places you can walk, there’s just one proper hiking trail, but we loved it so much, we felt it deserved its own entry. If you’re staying at the Mandarin Oriental, you can go with a guide—the trail is easy to follow, but it’s worth going with someone who can point out the flowers, reptiles, and more you might miss along the way. The trail starts just behind the old casino (a remnant of the island’s short-lived Trump era) and winds up a steep single track through thick forest—you’ll want a good stick for support; there are plenty to choose from at the trailhead—to the top of Mount Royal, the highest point on the island. On the way up you’ll spot orchids, turtles, and giant, tree-climbing hermit crabs. At the top, take a right toward the Mount Royal summit, and decide how far up the jagged boulder you’re willing to scale. You’ve got a stunning view north toward Mustique—but free one hand to take a picture at your own risk. Once you’ve clambered down off the rock (there is no…