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Known for generations as the Pink Princess, this legend opened its doors in 1885 and remains one of the largest and most celebrated hotels in Bermuda. Fresh off a $100 million renovation in 2016, the 170 rooms and suites are now what you’d expect from a Fairmont-managed property—clean, modern, and comfortably luxurious, all with water views—while public spaces have been elevated by an exceptional collection of modern art (Andy Warhol, Damien Hirst, and Ai Weiwei are just some of the luminaries who grace the walls). The new infinity pool has gorgeous views over the harbor, the spa offers treatments and fitness classes in partnership with noted brand exhale, and the marina’s water-sports team can organize everything from kayak and Jet ski rentals to paragliding lessons. Guests also have exclusive access to a private beach club on Sinky Bay—just 20 minutes away from the hotel via complimentary shuttle—which features water hammocks and snorkeling-friendly waters. Back at the resort, dining options include the buzzing Marcus, serving signature dishes from celebrated chef Marcus Samuelsson, and more casual options highlighting fresh seafood and local rum.

One of the iconic activities when visiting Jamaica is to raft along one of its rivers—particularly the long Rio Grande—and take in the island’s interior landscape. You can enjoy the Rio Grande’s range of flora and fauna during the relaxing, slow ride down its length. You’ll spot horses drinking along the riverbanks and plenty of tropical flowers and greenery, as well as locals cooling off near shore. Arrange your excursion with your hotel or an outfitter because you’ll need not only a raft but also a ride to the launch site at the mouth of the river, called Rafter’s Rest.

In the heart of Barbican, Kingston’s favorite “uptown” neighborhood, Uncorked started as a small wine and cheese shop but evolved into a sit-down wine bar with a menu that’s popular with the city’s professional crowd. Pick one of the tapas-style starters like the bacon-stuffed dates, or go all in and order one of the famous-for-good-reason gourmet burgers—including the Scotchie and Skellie, which is spiced Jamaican-style. The salads, seafood, and meat entrées don’t disappoint, either. All meals can be paired with the huge selection of imported wines, including vintages from Europe, Australia, and South Africa. It gets crowded at lunchtime, and tables are few, so come early to avoid a wait or stop in for evening cocktails and cheese and olive platters.

Why we love it: A design-savvy boutique hotel with direct beach access

The Highlights:
- Bright design that’s full of personality
- A focus on exploring the hotel’s natural surroundings
- Direct access to pristine Seven Mile Beach

The Review:
A welcome departure from the classic Negril resort scene, this stylish boutique hotel—opened in 2018—melds local flavor, a vintage Havana feel, and a contemporary sensibility in a way that speaks to the curious, independent traveler. Set along 220 pristine feet of Seven Mile Beach, the hotel features a clean-lined, mid-century modern-inspired aesthetic throughout, accented by bright textiles, artwork, and a curated soundtrack that celebrates the history of Jamaican music.

Room options range from studios set on the second floor of the accommodation wing, to options with patios or balconies looking out at either the garden or the ocean. All have air conditioning, USB outlets, Bluetooth radio, free Wi-Fi, and mini-bars. Skylark is big on encouraging guests to explore the area, whether that means taking advantage of the direct beach access (the hotel provides loungers, paddleboards, snorkeling gear, and beach games, plus food and beverage service), going for a boat ride, hiking to a waterfall, or zip-lining through the jungle.

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.

Set directly above rocky low cliffs of Negril and lit at night by torches and candles, Rockhouse Restaurant provides the setting for an elegant and romantic evening. (The setting’s pretty great during the day, too—breakfast, lunch, and dinner are served in this open-sided palapa and patio.) The New Jamaican cuisine means a refined and more health-conscious preparation of classic island recipes, with as many ingredients as possible from the hotel’s small organic garden across the road. Among the notable dinner offerings are the blackened mahimahi with mango chutney, snapper steamed in a banana leaf, and coconut shrimp.

Once a separate municipality, San Ángel—in the city’s south, nestled into its western foothills—is a leafy, genteel enclave whose relative isolation adds a soigné feel (for better or worse) you won’t find in neighboring Coyoacán. Ground zero for promenading is quaint Plaza San Jacinto, whose cute parish church (and beautiful cloister garden) is a sort of spiritual last stand amid the surrounding area’s high-toned consumerism. That said, the plaza’s true spirit comes alive Saturdays, at the so-called Bazar Sábado, an artisanal market that fills the area with stall after stall of handmade jewelry, textiles, crafts, and accessories, plus a great deal of art—some finer, some less so—in styles that go from hippie to haute. Strolling musicians and performers add to the carnival atmosphere.

Just next door to crowded Doctor’s Cave Beach in Montego Bay is a quiet and spacious stretch known as Cornwall Beach. You won’t see more than a couple of people at a time here during the week. Late afternoons and weekends attract a few locals who come to relax and enjoy the restaurant and bar. A small entry fee—under US$5—covers the on-site facilities, including lounge chairs and snorkel gear. Cornwall Beach occasionally hosts a sunset beach party on Sunday afternoons with a “bottomless” Appleton mug option (that is, all-you-can-drink rum).

Hotel June is a fairly new addition to L.A.’s hotel scene, but the historic Malibu spot, which re-opened in 2022 and was once home to Bob Dylan, has swiftly risen up the ranks. Why? For one, its minimalist design offers a calm, relaxing respite from the hectic Southern Californian lifestyle—while also paying homage to its ‘60s roots. There are only 13 bungalow-style rooms, and the vibe is strictly laid back. Private patios feature hammocks, a small pool invites you for a dip, and nearby beaches and trails offer outdoor exploration.

Cooked in an open pit over pimento wood, the jerk preparations here are all authentic and—according to most locals—the best on the island. Traditionally spiced chicken and pork, as well as a less fiery fish version, served in a tin container along with rice and peas and festival bread (akin to hush puppies). Getting your order to stay means eating while perched on wooden barrels, which certainly adds local flavor. While enjoying the delicious meal, you’ll get to observe the seemingly endless line of customers, and perhaps get a ringside view of a lively and noisy game of dominoes.

Standing at 3,793 feet, this towering, verdant peak is the island’s highest point. The dormant volcano is covered mostly in rain forest and capped with a cloud forest, making it ideal for a beautiful hike. The climb is an arduous one, however, and shouldn’t be attempted without a guide. If you manage to reach the top, you’ll be rewarded with sweeping views of St. Kitts, the Caribbean Sea, and neighboring islands like Nevis, Antigua, and Saba.

Baseball had nothing to do with the naming of Fenway Park: The stadium gets its moniker from the nearby Back Bay Fens, a stretch of saltwater marsh in the heart of Boston that was landscaped into a park by Frederick Law Olmsted. The Fens are among the wilder parts of the Emerald Necklace, 1,100 acres of parklands running from the Charles River to Brookline that include familiar spaces like the Boston Common and Boston Public Garden but also less-traveled (by visitors, anyway) sections like Olmsted Park, Jamaica Pond, the Arnold Arboretum, and Franklin Park. The arboretum, part of Harvard University and established in 1872, is one of Olmsted’s most unaltered terrains, with paths running up and around 261 acres of woodland interspersed with a curated collection of trees, plants, shrubs, and vines native to New England.

After opening in 2014, it didn’t take SALT Plage long to start appearing on lists of the world’s best beachfront restaurants. At the Christophe Harbour dining destination, guests gather on a palm-shaded deck overlooking White House Bay for craft cocktails and Caribbean fare, served from a corrugated steel bar that manages, like the menu, to project both a casual and sophisticated vibe. Live music and full-moon parties make this the place to be for sunset and beyond.

Despite the industrialized patty chain stores across Jamaica, the love for handmade patties continues in some parts of the island. Miss Sonia’s entrée-size, crusty patties are served at a small roadside restaurant across from the beach in Negril. She offers traditional fillings like beef or callaloo, as well as others like lobster and conch that she introduced at the suggestion of her numerous return visitors to Jamaica. When you get your order, be sure to shake on some of the secret spicy sauce—Miss Sonia won’t tell you what’s in it—and then dig in.

One of the perks of staying at the St. Kitts Marriott Resort is the opportunity to test your skills at the Royal St. Kitts Golf Club, an 18-hole, par 71 course laid out along the island’s Caribbean coast. If you’re not a Marriott guest, however, head to the Irie Fields Golf Course at Kittitian Hill, where organic farms fringe the fairways. Designed by World Golf Hall of Famer Ian Woosnam, the course is maintained without pesticides or chemicals—if you see a herd of sheep grazing on the back nine, let them play through.