Oracabessa Bay, Jamaica
The Jamaican mountains are the setting that inspired Ian Fleming to dream up James Bond—many of the books were written right here overlooking almond trees of the GoldenEye Villa. Despite the property’s storied past, it’s a casual, Caribbean-style luxury at GoldenEye: outdoor showers flanked by wide banana leaves, open-air architecture, and resolutely Jamaican cuisine—ackee, saltfish, plenty of bright fruit. The Fleming Villa is much as Fleming himself left it. Windows have no glass so you can catch the breeze; books are still heaped on the shelves; his writing desk invites you to come, sit, maybe bang out a few lines. The glassy water in the surrounding coves is made for kayaking, paddleboarding, glass-bottom-boating, snorkeling, swimming. The cottages and villas that frame the water’s edge—each sitting on their own acre—come with porches for private dining, claw-foot tubs, and gardens so green your eyes hurt.
Scotch on the Rocks
Coconut Grove, Ocho Rios
The hospitality offered by “Scotchie’s” close-knit team of five—cook, butler, waiter, housekeeper, and gardener—is unmatched in Ocho Rios. Head chef Cherry consults with guests daily to craft seasonal menus that take into consideration dietary intolerances and food sensitivities. Rooms in this villa are impeccable, with high-quality linens and beautiful details, but the best feature of this five-bedroom house is its location. It’s right on the edge of a cliff, hovering above the White River Fish Sanctuary coral reef. Wake up early—sunrise over the Caribbean Sea from your bedroom window should help—and start the day with kayaking, paddleboarding, or snorkeling (all your gear is provided).
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.
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.
The resort is known for having the same feel now as it did when it opened (when Sir Winston Churchill used to come here to paint). Colonial-style cottages offset the tropical beachside setting that has a bit of a retro Jamaican feel—and there's croquet on the lawn. Blessedly, there are no TVs to be found. The rooms are as on the beach as it gets (open the door and step in sand) and they are happy to bring you breakfast on your veranda if you don’t feel like making it over to the palm-covered dining room.
Fair Prospect to Folly Rd., Anchovy Gardens, Port Antonio
You can be as private or social as you like at this resort, which feels like a village of waterfront villas. Most people spend the day lounging by the infinity pool overlooking the sea, but you can relax by the private pool in your villa for a more secluded experience. The rooms are newly refurbished, simple, and modern, keeping the gorgeous setting the focus, with features like outdoor soaking tubs and sun decks. The town of Port Antonio, where the resort is located, was a hotspot in the 60’s and part of the experience is checking out the restaurants, bars, and live music in town. Fun feature: If you get tired of the beach, there’s a screening room that you can reserve.