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Sugar Ridge is much about the view. One of those rare Caribbean hotels that doesn’t sit at the edge of the sand, this boutique luxury resort, ranging up a hillside on Antigua’s west coast, not only overlooks palm-lined beaches and the marina at Jolly Harbour but also looks out across the greens and blues of the Caribbean toward St. Kitts, Nevis, and Redonda. The rooms, in clusters of four, two upstairs, two down, are Caribbean modern, with a focus on the four-poster, netting-draped, king-size beds. There are two restaurants, two pools, an Aveda Spa, and a fitness center so large it’s almost as if they were expecting a sports team to show up. And beach lovers fear not. A complimentary shuttle will have you down to the shore in minutes.

What’s old is new again in Saint-Pierre, a city built under majestic Mount Pelée on Martinique’s Caribbean coast. In 1902, Mount Pelée volcano erupted, leveling the city and killing all 30,000 inhabitants– save one lucky prison inmate, whose thick cell walls protected him from the blast. Today, the rebuilt Saint-Pierre honors its fiery past at the Musée Volcanologique, a mini-Pompeii filled with carefully preserved relics. History meets modernity at the southern entrance where seven inspired, contemporary Caribbean artists have created 32 colorful totem sculptures welcoming guests. There are also popular dive sites nearby, where scuba divers can swim alongside century-old wrecks of ships that sunk in the explosion.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

Lemongrass restaurant is one of Oslo’s only Caribbean restaurants. Their food is inspired by the French, Spanish and British colonial history throughout the Caribbean, and they offer everything from bouillabaisse to jerk chicken and curried goat. Located next to Nasjonalgalleriet (the National Gallery) and just a stone’s throw from Oslo’s high street, it makes for a satisfying tropical meal when the winter cold sets in.

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.

Music producer turned hotelier Chris Blackwell has made a name for himself converting Caribbean properties (Pink Sands on Harbour Island, GoldenEye in Jamaica) into jetset destinations with studios where his rock-and-roll friends can kick back while recording their next album, but it all began at Compass Point. Bob Marley, the Rolling Stones, and Eric Clapton have all stayed in some of the resort’s 18 rainbow-hued stand-alone huts, which are inspired by the colors of Bahama’s Junkanoo carnival and are simply furnished to encourage engagement with the outdoors; though the interiors are air-conditioned, most have sea-view balconies that are sighted to catch ocean breezes. In keeping with the theme, each comes with a surround-sound system and a library of CDs by artists who have recorded at Compass Point, but you’re just as likely to keep them off, preferring instead to listen to the waves that crash on the hotel’s small beach.

Sometimes the best way to cool down in the Caribbean is to heat things up! And nothing spells relief like a dip in the Ani Villas hot tub – perched on the edge of a cliff overlooking secluded Little Bay Beach, Anguilla.

Tayrona National Natural Park has become such a popular destination during typical vacation periods that authorities have had to limit admission. But an off-season visit offers singular luxuries like miles of all-but-solitary beaches, jungle trails, and a unique way to observe a variety of monkeys and tropical birds in every brilliant hue. Tayrona can be experienced as a day trip from Santa Marta or as a several-night stay at one of the park’s accommodations. From the main entrance at Cañaveral (El Zaíno), visitors can take a leisurely hike to the ocean while a donkey handles the luggage; horses are also available for those who prefer not to walk. This same park entrance also leads directly to high-roofed, native-wood cabins known as ecohabs, a slightly fancier option for staying in the park.

Willemstad’s first colonial settlement started as a hub for Dutch slave traders. Now a World Heritage site, this modern city center has a distinct Euro-Caribbean atmosphere, its preserved colonial buildings housing fashion boutiques, art galleries, and sidewalk cafés. Wander down Punda’s narrow cobblestoned alleys, then snap a signature photo at the Queen Wilhelmina Park’s giant Curaçao and Dushi signs. The neighborhood gets extra lively during the free Punda Vibes event every Thursday from 6 p.m. to 10 p.m., featuring an outdoor market, live music, and local folkloric dancing.

More than any other of the luxury beach-colonies that opened in Jamaica in the 1950s, Tryall has retained the feel of a private club. Yet this 2,200-acre property, with 87 villas, almost all having views that sweep down to the Caribbean, is Jamaica’s largest all-villa resort, and home to one of the Caribbean’s finest golf courses. Created by a group of Texas investors that included a future governor (John Connally) and future senator (Lloyd Bentsen), the resort, backing its own private beach just west of Montego Bay, continues to add villas notable for their luxury and individuality, one with a gallery devoted to Jamaican art, another with its own basketball court. Each villa has a dedicated staff, including a chef, housekeeper, butler, laundress, and gardener. And although each villa is essentially self-contained, the resort’s restored 1834 Georgian Great House, with its restaurant and bar, where events such as the manager’s cocktail party are held, serves as focal point for guests who want to “get out” without leaving the property.

If you were to picture the perfect Caribbean beach, it would probably look something like Salt Whistle Bay on Mayreau. Here, clear, turquoise waters lap at 2.5 miles of sparkling white sand, while palm trees, seagrape plants, and flowering bushes provide shady spots for lounging. At one end, you can walk the few yards of land that separate the Caribbean and Atlantic sides of the island. The only catch is that you’ll need a boat to reach the beach, so rent your own or book a day sail to Mayreau.

The Caribbean’s first long-distance hiking trail runs 115 miles south to north. Fourteen segments break Waitukubuli into manageable day hikes—important for rule-followers, as camping is tolerated but not technically legal in Dominica’s reserves and national parks. Brace for lofty peaks, precipitous valleys, and riotous tangles of rain forest vegetation on this trek, which bears the island’s original indigenous name, meaning “tall her body.” Consider hiring a local guide for expert advice on trekking the steep, corrugated landscape, which Christopher Columbus once described by simply crumpling up a ball of paper.

A visit to the incredible 365-island archipelago (also called the San Blas Islands) within the communal lands of the Guna Yala indigenous nation provides some extraordinary seaside experiences. The islands making up the outer archipelago are unspoiled and feature gorgeous white-sand beaches, turquoise seas, and a one-of-a-kind encounter with Guna culture. Visitors lodge in natural-material huts (cane walls and interwoven palm-frond roofs) or—if you’re in the mood—sleep under the stars in palm-strung hammocks. Local women sport colorful dress made in the style known as mola, a traditional Gula artisanal weaving technique. A highway was built several years back that lets you travel from Panama City to Puerto de Cartí in as few as two hours.

Sometimes you have to be a tourist to enjoy the great pleasures that travel offers. That’s why a visit to Mountain Top on St. Thomas is a must-do activity for any visitor. In 1949, a British restaurateur began a mission to develop the best Caribbean libation. He finally settled on the now-famous banana daiquiri, which he first mixed on St. Thomas. The drink is still served up daily using the original ingredients at Mountain Top, an emporium of souvenirs and kitsch. Just walk through the mountains of t-shirts to enjoy both the drink and, honestly, one of the best views on the island.

The Antigua Yacht Club is the center of so much of Antigua’s world-class sailing experience. Right in the heart of English Harbour, this prestigious yacht club has been serving the island for over 40 years. It hosts the Classic Yacht Regatta, the RORC Caribbean 600, Sailing Week, the National Sailing Academy that serves the community with free watersports education, and even the Caribbean Dingy Championships. This is the place to stock up on last-minute supplies at the shop, or grab a bite at Cloggy’s or Club Sushi. Yeah, The Antigua Yacht Club is a hub for sailors of all stripes to talk shop whether coming in or leaving for some time on the water.