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.
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).
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.
Tamarind Beach Hotel
The big draw at the Tamarind Beach Hotel is the beach—glittering, talc-soft white sand with the bright blue of the Caribbean Sea on one side and lush, palm-tree-dotted tropical gardens on the other. The sheltered bay is a popular mooring for smaller sailboats (mega yachts post up on the southern tip of the island, where a new deep-water marina has been built off of Glossy Bay), and the hotel has a well-stocked deli for reprovisioning. For land-based overnight guests, there are thirty-one rooms and eight beachfront suites. The bedrooms are breezy and comfortable with hardwood floors, walnut-and-white-paneled walls, comfortable beds, and a balcony or patio opening onto the beach. There are two restaurants, a beach bar, and a spa, as well as kayaks, windsurfers, paddleboards, and snorkel gear. The hotel also enjoys reciprocity with the Canouan Estate, should guests wish to play the golf course or visit the restaurants there.
Mandarin Oriental Canouan
Carenage Bay, Canouan
Located on a picture-perfect stretch of Godahl’s beach on the Atlantic side of the island, the Mandarin Oriental takes full advantage of the sweeping views out over the water. The hotel’s twenty-six colonial-style suites and thirteen villas all face the ocean; ground floor suites have individual access to the beach, and those on the upper level have balconies overlooking it. The rooms are done in a palette of creams with dark woods and fuchsia accents, and each is equipped with every luxury you could wish for (walk-in closet, indoor and outdoor lounge areas, Nespresso machine, Acqua di Parma toiletries, blackout shades, yoga mat, beach bag, your own personal butler) as well as a quite a few you’ve never thought of, like an iPad that controls nearly everything in the room. The pink lounge chairs on the beach and by the infinity pool are perfect for a morning of doing nothing. Then grab lunch at the pool bar—the conch ceviche or the shrimp tacos is the way to go. The hotel is on the Canouan Estate, with access to five different beaches (some on the Atlantic and some on the…
El Blok Hotel
158 Calle Flamboyan, Vieques
Inspired by the coral reefs surrounding Vieques, El Blok’s unusual Brutalist architecture comes courtesy of Puerto Rican architect Nataniel Fuster. Natural light and fresh air flit through the round cutouts of the concrete walls, creating shadows to mimic the feeling of being underwater. The four-story building curves around an oval atrium, meaning there are no hard angles to be found in the twenty-two spacious one-bedroom suites. Minimalist in nature, each room is a playfully designed mixture of texture and light, featuring sleek furnishings and lightweight cotton linens. Upstairs, El Blok’s swanky rooftop bar and infinity pool draw live bands, DJs, and a crowd of local hipsters. Skip across the street to the Vieques beach, where you may be able to catch sight of some of the wild horses that roam the island.
The Villas at Stonehaven
Stonehaven Bay, Black Rock
Architect Arne Hasselqvist constructed these fourteen villas from a medley of well-sourced materials: greenheart hardwoods from Guyana, oil-ribbed bronze hardware from Peru, granite and marble countertops from Brazil. The finished product is a seamlessly integrated design that channels the old-fashioned glamour of a Caribbean manor house. The villas—which range in size from a one-bedroom with a king-size bed to a four-bedroom that can accommodate seven adults—each come with an infinity pool, private gardens, and panoramic sea views. Breakfast can be cooked in your private kitchen upon request, and the Pavilion Restaurant is always a solid bet, serving Caribbean and American fare in a lush garden setting.
Hyatt Regency Trinidad
1 Wrightson Rd., Port-of-Spain
The go-to for a luxurious stay in Trinidad, the Hyatt Regency shines with a seaside location in the heart of Port of Spain. Rooms are sleek, with white oak floors and plush but firm bedding. Waterfront and city views are salves to the eyes but easily avoided during early mornings with blackout curtains and noise-blocking walls. Downstairs, the Waterfront bar and restaurant offers a complimentary breakfast service, a sushi bar, and café. Take a seat on the outdoor patio for undulating sea waves over plantain chips and coffee. Upstairs, the hotel pool offers a stunning view of the city, and the nearby spa can take care of any bodily woes with a menu of mani-pedis, facials, and deep-tissue massages.
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