F&W's favorite Caribbean hotels include La Samanna in St. Martin. Photo courtesy Orient Express Hotels Oprah and Jackie O have stayed at this iconic Caribbean hotel, where all 83 rooms have a view of the ocean and private white-sand beach. A recent renovation has added comfortable cabanas and two restaurants—one beachside-casual, one high-end French. At the latter, chef Gil Dumoulin, of Paris's famed Les Ambassadeurs, cooks Caribbean-inflected dishes like foie gras with mango. Guests can book the table in the candlelit wine cellar—at 12,000 bottles, the largest in the Caribbean—where sommelier Christian Mirande leads wine-and-cheese tastings and staffers pour local rums. Doubles from $445; lasamanna.com
At this property on an 850-acre private island, the gregarious staff is part of the charm: A resident scientist leads walking tours to see rare species like the rock iguana, and the gardeners are known to recite Chinese poetry. The newest addition is an El Bulli-trained head chef, Xavier Arnau, whose dishes, like apple gazpacho with shrimp, incorporate local fish and fruit from the organic orchard; he also plans to harvest winter vegetables from a new greenhouse. There are 15 cottages and four villas to choose from, half of which were just renovated. Doubles from $695; guana.com
After kayaking through the adjacent 5,000-acre Espíritu Santo nature reserve, guests at this sprawling, palm tree-dotted golf resort can watch a Champagne-sabering ceremony or have dinner at the Jean-Georges Vongerichten restaurant Fern. The menu is Asian-influenced—hamachi sashimi, grilled tenderloin with gingery shiitake mushrooms—with nods to local flavors in dishes like octopus with ají dulce, Puerto Rico's ubiquitous sweet peppers. After dinner, guests can head back out into nature, to the glowing bioluminescent bay in Fajardo. Doubles from $830; stregisbahiabeach.com
At this stylish hotel, French touches are everywhere: The gift shop sells Parisian lace dresses, the 40 newly revamped rooms incorporate vintage French fabrics and the ambitious wine list includes Burgundies from Chambertin, Puligny-Montrachet and Meursault. Villa guests are greeted with a bottle of Veuve Clicquot, and on Fridays, sommeliers lead Champagne tastings that include rare vintages of producers like Billecart-Salmon. The menu from chef Yann Vinsot (who trained at Burgundy's L'Espérance) combines French mainstays like sole meunière with Caribbean-inspired dishes like wahoo ceviche with coconut milk. Doubles from $675; isle-de-france.com
At the island's newest boutique hotel, the chefs bake bread, dry-age steak and cure bacon. Local ingredients like conch and spiny lobster appear frequently on the five-course winter tasting menu, which the staff will serve right on the beach. Each of the 21 enormous, shabby-chic suites has a beautiful, all-white kitchen. Suites from $594; beachhousetci.com
The Jamaican town of Port Antonio is constantly reinventing itself: In the 1950s it was a favorite hangout of movie stars like Errol Flynn, and before that it was known as the birthplace of jerk cooking. Now British music mogul Jon Baker is reviving it again. In December, Baker overhauled the 13-villa Trident Hotel, making it super-mod with the help of a young Jamaican architect, Vidal Dowding. "In the music industry, I've prided myself on developing new talent, and I applied that approach to finding our architect and our chef, both around 30," says Baker, who also runs the nearby resort Geejam. Trident's youthful vibe shows in playful touches like ultra-curvy Vitra Verner Panton chairs and eccentric animal sculptures; the food focuses on Jamaican-Japanese dishes like jerk sushi rolls. Baker also modernized the adjacent castle,the estate of former Trident owner Earl Levy, with additions like Apple TV; guests can take over the whole property or book one of its eight rooms. Next year, Baker will reopen the nearby Blue Lagoon restaurant, another onetime celebrity haunt. Hotel doubles from $600; castle doubles from $250; geejamcollection.com
Negril is known as a party town, but travelers come to this mellow resort to relax and unplug: The 18 thatched-roof, seaside cottages have no televisions. Local chefs lead jerk-cooking tutorials; guests can also tour a rum distillery, take yoga classes or get fresh coconut body treatments in the gardens. Doubles from $300; thespajamaica.com
Fed up with the fashionista crush of St. Barts, the artists Brice and Helen Marden decided six years ago to escape to Nevis and purchase this serene property 1,000 feet above the sea. "It was built in the 1800s as a sugarcane plantation, but I try not to focus on that," Helen says. "I took down a painting of people cutting cane. It's by a famous painter, Eva Wilkin, but I didn't want that hanging in the resort." Instead, she selected pieces by René Ricard and Darren Almond. The couple took over full ownership last year and, with the help of Miami landscape designer Raymond Jungles, began planting gardens. These now provide peppers and herbs for the cocktails, chutneys and sorbets served at their outdoor restaurant, overlooking spring-fed waterfalls. Chef Ricky Finch, a local, uses recipes from the couple's daughter, Melia Marden, the chef at The Smile restaurant in New York City. Doubles from $180; goldenrocknevis.com
Since the late '80s, when Island Records founder Chris Blackwell opened this boutique property (the former home of James Bond author Ian Fleming), he's steadily added villas with quirky amenities, such as retro-style Smeg refrigerators stocked with Red Stripe beer and sound systems that play tracks he produced for U2 and Bob Marley. Visitors can now take day trips to Pantrepant, Blackwell's private residence and sustainable farm, where they can gather produce like bok choy and oranges (which show up at all three of Blackwell's Jamaica resorts) or even milk a cow. The day ends with a Jamaican feast at the farm prepared by Blackwell's private chef, known as Mama J. Doubles start at $560; goldeneye.com
On the lush West Indies island of Dominica, Secret Bay's four cedar and Guyanese wood residences are built cleverly into the cliffs and trees à la Swiss Family Robinson—but with access to private chefs and modern kitchens with well-stocked wine fridges. The property is not a traditional hotel—there's no front desk or restaurant—but the concierge sets up experiences for each guest, arranging meals, in-villa jazz concerts and open-sea fishing excursions in a traditional wooden canoe (the fish can be prepared for dinner en suite by a local chef). Doubles from $402; secretbay.dm
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