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A signature experience in Negril is to go on a two-hour glass-bottom boat snorkel trip, toward the cliffside or to the nearby reef around Booby Cay. Truth be told, snorkeling isn’t a must if you’re not up for it—but floating on a small boat amid deep jade and turquoise waters and being able to see marine life 20 feet or more below through the glass is a memorable experience. If you do want to snorkel, the cliffside has stunning limestone formations and underwater caves, while the reef is filled with all sorts of marine life, from stingrays to barracuda. A glass-bottom boat ride shouldn’t cost you more than US$20 per person. Look out for Famous Vincent‘s boat—the best pick—or approach one you see resting along Seven Mile Beach, across any reputable resort. The boats—including Famous Vincent—occasionally ride along the cliffside resorts in the mornings or afternoons, looking for anyone interested in an impromptu adventure.

Remember the oldie “Under the Boardwalk” by The Drifters? The owner of Drifters Bar, Luddy Samms, tells stories of his career with The Drifters, as well as tales of singing with Eric Clapton and Stevie Winwood and Bruce Willis. Samms opened this hot-spot bar and performance venue on Seven Mile Beach in 2011, and expats, locals, and tourists flock here for cold Red Stripe, good food, and lots of live music in a variety of genres. Because this is an authentic Jamaican beach bar, though, reggae is king.

Action-packed Hellshire Beach, the easy beach choice for many Kingston residents, is lined with dozens of wooden food shacks. Aunt May’s is a solid pick for a classic Jamaican beachside meal, serving fresh fish with festival (fried dumplings) or bammy (cassava flour flatbread), lobster, and other seafood. Hellshire is particularly busy on weekends, when locals take a break from their workweek, and sees relatively few tourists, so it has an authentic Jamaican vibe like few other beaches.

There’s a reason Blue Cave Castle (affectionately dubbed “BCC” by return visitors) has a following. Designed in the shape of a castle, it’s impossible to miss this dominating blue structure on Negril’s cliff side. Tower rooms offer dramatic views 50 feet above the sea, and yet surprisingly, rates start at $50 night and go up to only $120 for a stunning 2-floor “penthouse” suite on the top floor. Blue Cave is one of the West End’s best-kept secrets. Going to sleep in a castle to the immediate sound of crashing waves is a unique experience. Even if you don’t get to stay here, be sure to stop by the on-site Hideaway Eatery, owned and run by Chef Teddy, for a delicious lobster dinner.

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.

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.

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.

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.

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.

A reflective site for Marian believers, these stone caverns function as a New World counterpart to the famous French shrine to Our Lady of Lourdes, where it’s said the Virgin Mary’s apparition once appeared. You’ll marvel at the naturally formed twin grottos, positioned across the road from each other, as well as the oversize statue of the Virgin Mary, which weighs in at 1,500 pounds. A priest named Erkamp and his parishioners placed the imposing icon here in 1958.

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.