144 One Love Dr., Negril
Comprising a handful of Caribbean-blue villas nestled in the limestone cliffs of Jamaica’s west coast, the Caves benefits from one of the best locations on the island. Each one- or two-bedroom cottage is fitted with tasteful wooden furnishings, stained-glass windows, and hand-dyed fabrics. For larger groups, the Clandestino, a three-bedroom villa under a thatched roof, offers a private pool, a hot tub, and a sauna. Not all of the cottages have sea views, but those that do will bring you so close to the endless expanse of water that it feels as if you could jump in from your back door. In fact, beach access requires a leap of faith—guests climb ladders, ranging from five to thirty-three feet, to jump off the cliffs into the warm sea below. The staff is well-versed in everything related to the ocean and can guide you through a snorkeling adventure while providing amazing detail. For breakfast, the Gazebo serves Jamaican and American items like callaloo, ackee, and saltfish, as well as fresh banana pancakes and omelets. At night, stroll down a coral staircase to the Blackwell Rum Bar, carved out of the…
Blue Lagoon, Port Antonio
Kanopi blends seamlessly into its environment, a compound of tree houses hidden deep in a grove of hundred-foot Banyan trees, bamboo shoots, and ginger lilies. In fact, it was built with such consideration for its environment, the one tree on the property that was cut wound up being repurposed into a set of dining tables. Floor-to-ceiling doors fold away to reveal the dramatic rain forest foliage that seems to practically climb its way indoors. Each tree house feels intimate and romantic, with crisp white linens, handcrafted wood furnishings, and vibrant artwork, all made by local artisans. For food, Kanopi relies on local produce like plantains, breadfruit, sweet potatoes, and fresh papaya from the surrounding forest. For all its rural charm, it’s also just twenty minutes from Port Antonio, so the perks of city life are easily accessible during the day, before you return to your private rain forest hideaway at night.
Oracabessa Bay, St. Mary
Born from the imagination of James Bond novelist Ian Fleming, GoldenEye is rooted in such cultural lore, it’s hard not to feel like you’re playing a part in a glamorous spy story. It was here Fleming penned all fourteen Bond books (the author’s home, the Fleming Villa, can be reserved separately), and this is also where Bond’s cinematic debut, Dr. No, was filmed. But if these cultural muses don’t inspire a trip, consider that the collection of villas was also constructed by an all-star cast. Chris Blackwell, the founder of Island Records, enlisted Ann Hodges, one of Jamaica’s most noted architects, to produce the property’s supremely comfortable accommodations, fitted with hardwood floors, outdoor showers, and lush, secluded gardens. Go for one of the six lagoon cottages, which were built to hover above the tranquil water and have private docks for midnight swims and morning paddleboarding. In the spare, octagonal bedrooms, louvred windows welcome natural sea breezes to replace air-conditioning.
Road View, St. Peter
Cobblers Cove reminds us of a tropical country club: Keep the pastels, vintage florals, and starched white linens of a Slim Aarons photograph, but add in the warmth of a friendly staff, a gorgeous sea view, and a stiff rum punch. The 1940s mansion has drawn guests through its powder-pink walls for decades, thanks to the impeccable service and a restaurant often hailed as the best on the island. The charming room décor includes white bamboo seating, Egyptian cotton bed linens, goose-down pillows, and an absence of televisions. Stimulation comes the old-fashioned way: a jaunt on the easily accessible beach, where snorkeling reveals turtles darting among coral, or an indoor game of chess or checkers inside the wood- and leather-accented dining hall. Time dinner to catch the sunset, when the golden light illuminates the walls of the Camelot restaurant, where Bajan chef Jason Joseph grills the catch of the day to perfection.
Dunmore St., Dunmore Town
The result of a masterful renovation and takeover by the luxury adventure collective, Eleven Experience, Bahama House is tucked into a restored 1800's pale-pink painted stone building in the heart of Dunmore Town.
The Other Side
There’s plenty to do on the property, including morning yoga, paddle boarding, diving into swimming holes or even tend to the on-site vegetable garden if you wish, but you can also just relax at the swimming pool, which is pretty enticing on its own.
Playa Grande Beach Club
Maria Trinidad Sanchez Province, Playa Grande
On Dominican Republic’s slightly more wild north shore, interior designer Celerie Kemble and her financier husband wanted to create a low-key beach retreat that had the intimacy of a friend’s private home. Here, Kemble applies her playful aesthetic, a kind of Palm-Beach-meets-island-living-vibe to the immaculate grounds: there are high-back wicker chairs, ikat throw pillows, copper bathtubs, seagrass rugs and cane furniture. Each white-washed bungalow (there are six one-bedrooms and three three-bedrooms, best suited for families traveling together) has its own distinct feel and is lovingly curated with vintage pieces Kemble has hand-picked on her travels as well as those designed by local craftsman. Cool lattice-framed cabanas dot the lap pool, should you tire of the views on the mile-long private beach. Come evening, much of the activity centers around the Beach Club, which serves up a Caribbean-inflected menu and, of course, strong cocktails and a lively atmosphere.
Anse de Toiny, St. Barths
Though it's undeniably fun, St. Barths isn't traditionally the most quiet, or secluded, place for a honeymoon—which is exactly what makes Le Toiny, a recently renovated haven a healthy distance from town, so appealing. There are only 14 suites here, each with a view of the ocean and its own private pool, and the intimacy means the high-touch, Relaix & Chateaux-trained staff is available to tend to your every need, whether it be organizing a romantic beachside dinner or loading you into a Jeep Wrangler for a ride to the tennis courts. The décor, expertly handled by designer Bee Osborn, is comfortable and neutral, with beachy accents like roped door handles and reclaimed wood side tables. The restaurant and suites here are up on the hillside for better views, but the water access is still potentially one of the island's best: A short walk (or ride in one of those Jeep Wranglers) will land you at the brand-new private beach club, with a full bar, hammock, beach chairs, and a shop stocked with coverups, tanning oil, and other beach essentials.
New Castle Rd., Kingston
This is another Chris Blackwell property (the other is GoldenEye), and as the founder of Island Records, Blackwell keeps the walls of these white wooden cottages lined with an array of historic rock-and-roll memorabilia. (This is the place Bob Marley chose as an escape when he faced threats to his life in the mid-1970s.) It feels like a secluded mountain village tucked high in the contours of Jamaica’s Blue Mountain Range, over 3,000 feet above sea level. The nineteenth-century Georgian architecture has a sophisticated, laid-back charm, matched by hand-dyed batik linens and four-poster beds with billowing drapes. And it’s almost a magical experience to stroll through the morning mist in the private gardens before breakfast. The hikes (led by expert staff members) give you a real sense of what the interior of the island is all about; afterward, unwind with an aloe wrap at the spa. But our favorite thing to do was to take in the views—every last heart-stopping one of them.
Queen's Hwy., Gregory Town
The only international property from the Enchantment Group (a.k.a. the good people who brought us Mii Amo), The Cove delivers on everything you'd want from a Caribbean vacation, starting with the pristine white sand, which you'll find in spades at the protected, private cove it occupies. The tranquil rooms, decorated in soft, gentle whites and neutrals, feature sliding doors that open directly out to ocean views framed by swaying palm trees. At 57 rooms, The Cove is much more intimate than their namesake resort, though it's unsurprisingly kitted out with an incredible infinity pool and spa. There are two excellent restaurants (and a wonderfully lazy bar) on site, but should you want to venture further afield, the candy-colored town of Harbour Island is a short ride away, and concierge can also organize every adventure imaginable, from kayaking to fishing to sailing.
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