"Boaters looking to trade the open seas for dry land have plenty of reasons to dock at Union Island’s Anchorage Yacht Club. The 1975 stalwart, which was renovated in 2018, offers a collection of understated rooms and cottages overlooking a small marina and white-sand beach, where you can catch some serious airtime during a three-day kitesurfing intensive at the on-site center. Don’t have a skiff of your own? The staff can arrange for catamaran tours of nearby Tobago Cays or deep-sea fishing trips for mahi, tuna, and amberjack, all of which make appearances at the hotel’s waterfront restaurant depending on the daily catch. Before you turn in for the night, order a rum punch under the stars at the thatched-roof bar next door."

"With its own shuttle flight service from St. Lucia andBarbadosand an unbeatable location on one of the Caribbean’s most picturesque stretches of sand, Bequia Beach Hotel is an island unto itself. The 10-acre property, easily Bequia’s most luxurious, also includes a spa, two swimming pools, two restaurants, and a canvas-tented bar on nearby Princess Margaret Beach, plus 56 individually appointed rooms and suites furnished in an eclectic, island-chic style (think red four-poster beds, wicker armchairs, and palm-accented throw pillows). Adventurous types can take advantage of the hotel’s free sports equipment (including kayaks, paddleboards, and bikes), while those who prefer more subdued activities can opt for complimentary yoga classes."

"If you want to vacation like British royalty, visit the mosquito-shaped island of Mustique, which Naomi Campbell, Mick Jagger, and Princess Margaret have all called their home away from home. Once on land, there’s no better place to stay than the Cotton House, a private retreat that feels like the lap of luxury. Set on 13 acres of cerulean beachfront and gardens thick with jasmine and frangipani, the 20 rooms and suites are awash in neutral hues inspired by their surroundings, with wicker pendant lighting, ikat throw pillows, and breezy mosquito nets over the beds. Explore the coral reefs near the shoreline in a glass-bottom kayak, or improve your backhand with help from the resident tennis pro. After a day of sun-soaked adventure, dine on fresh-caught specialties (pan-seared barracuda, Caribbean-style sushi) at Veranda restaurant, then retire to the Great Room, a colonial-inspired lounge offering rare and local rums."

"Located just two miles north of Port Elizabeth, on an 18th-century sugar plantation and working sea salt farm that overlooks Spring Bay, Firefly Bequia has all the sophistication of its sister accommodations on tony Mustique. Scattered along the hillside to maximize ocean views, the four suites and one two-bedroom cottage are outfitted with king-size four-poster beds, indoor-outdoor showers, and rattan ceiling fans that recall the island’s colonial past. Though it’s a five-minute walk to the beach, you’ll spot the remnants of the plantation’s original sugar mill, a croquet lawn and swimming pool, and the hotel’s resident goats along the way. Upon your return, a cocktail in the stone bar, where green bananas hang like chandeliers, is just the thing to ease you into a star-filled night."

"In the Caribbean’s Windward Islands, a string of some 600 islands and islets dot the sea between St. Lucia and Grenada. It’s a paradise for yachters, where you can drop anchor off an uninhabited island and live out your Robinson Crusoe fantasies. A handful of these islands are home to resorts, including the private Palm Island, first leased to an American couple in 1966 for $1 per year. They established the ten-room Palm Island Beach Club, which over the years has grown—though there are still only a total of 43 guest rooms on this single-resort island. Sponsored by Elite Island Resorts"

"Serenity is easy to come by on the private-island resort of Petit St. Vincent, a 115-acre property from the 1960s. It recently underwent a multimillion-dollar renovation but retains its original charms—there are no cars or in-room televisions (and don’t even think about WiFi) in the 22 cottages and suites, and anything you might need arrives at your doorstep with the simple raise of a yellow flag. A Balinese-inspired spa soothes the body, while two open-air yoga pavilions quiet the mind. If you’re looking for more action, you can explore the island’s pristine reef formations with expert divers through Jean-Michel Cousteau’s only Caribbean scuba center, or rent one of four yachts to catch local mahi mahi—then have the chefs prepare it for you beachside back at the resort."

"Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice."

"While most of the Grenadines’ most luxurious hotels cater to the one percent, Salt Whistle Bay, on Mayreau, offers a blissfully pared back—though no less exclusive—experience. You’ll feel like a modern-day Robinson Crusoe when holed up in one of the 22-acre property’s eco-friendly bell tents or stone bungalows, each outfitted with colorful rugs, fans, and plush linens, and positioned to capture ocean breezes. By day, swim with sea turtles, sting rays, and tropical fish in the surrounding reef-filled waters—snorkeling masks are free to guests, as are stand-up paddleboards—or try kiteboarding on the resort’s designated beach. By night, share those adventures over a dinner of grilled lobster at the on-site restaurant and bar."

"Unsure if Sugar Reef Bequia is right for you? Take the hotel’s online “Go or no” test. Guests expecting air-conditioning should stay home. Those who like “dancing with locals and tasting exotic fruits” should book now. Ideal for a grown-up getaway (guests must be 18 or over), the hotel is set on an 18th-century coconut plantation that borders the beach. The estate’s two original buildings hold eight guest quarters. Local fishermen and farmers supply the restaurant with ingredients for dishes such as lobster roti. Get to know the island on a hike with a local historian or over Ti’ Punch with the hotel’s bartender."

"At Tamarind Beach Hotel, the 31 beachfront rooms feature castaway-chic furnishings, a sea-inspired palette, and island-appropriate décor, while the eight ocean-adjacent suites take their cues from Canouan’s colonial past. Once settled in, spend your days golfing on the Jim Fazio–designed championship golf course, hiking to the top of Mount Royal (the island’s highest point), plying the turquoise waters via catamaran or sailboat, or indulging in a coconut-and-brown-sugar scrub at the spa. Whichever you choose, kick off the evening with a rum sundowner served under a palapa at the Beach Bar."

"Even though it’s just 200 yards off the coast of St. Vincent and accessible via a two-minute ferry ride, Young Island feels worlds away from the cares of mainland life. The resort’s 29 guest cottages, which are outfitted with tropical-chic wicker furnishings, stone walls, and louvered windows, provide a plush landing spot after days spent diving among sea turtles and sea horses, hiking neighboring trails to spot the ruins of Fort Duvernette, and swimming up to the Coconut Bar, located on a floating platform 30 feet offshore. Each week, the on-site restaurant serves up Caribbean barbecue favorites like pigeon-pea-and-pumpkin stew, corn fritters, and molasses-glazed wings, making for a delicious stay."