Establishment neighborhood
Round Hill
John Pringle Dr., Montego Bay
Round Hill has long been a landing spot for starlets and artists: Grace Kelly, Alfred Hitchcock, Ian Fleming, Oscar Hammerstein, the list goes on. The Kennedys took their honeymoon here. But it’s Ralph Lauren (he bought a home here in the ‘80s, and describes the property as Eden) who’s left an indelible mark on the place: He designed the rooms. The resort leans more recreational than relaxed. Tennis is a fixture here, and if you time your visit right, you can attend clinic with a big-name player. A resort staffer will teach you to sail a Hobie Cat and leave you to whip over the waves. Water skiing? Glass-bottom boating? You’ve got it. And for little vacationers, there’s a nanny program and a kids club with a loaded calendar of activities, which changes daily.
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).
The Caves
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…
Kanopi House
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.
Zimbali’s Mountain Cooking Studio
Canaan Mountain, Negril
The staff at Zimbali, a twenty-minute drive east from Negril, hold a theory that Jamaica gets more interesting the farther out you get from the cities, and the eco-friendly retreat makes a strong case. It’s attached to a seven-acre organic farm, and the abundance of Jamaica’s bounty is delivered fresh and prepared exquisitely. The dinner begins with a blended juice made of fruit picked straight from the soil or tree, and then a guided tour of the land that grows the ingredients for the night’s meal. Then sit at the counter and watch the chef create a six-course culinary journey, with bowls of pumpkin soup, jerk shrimp, and perfectly seasoned fish wrapped in banana leaf. Try to snag a table on Wednesday night when African drummers provide live entertainment.
Stush in the Bush
Free Hill, Bamboo
Jamaica’s Rastafari prescribes a vegetarian-friendly, alcohol-free diet that strips food of all additives and preservatives to harness the life energy that runs through us all, and it birthed a food movement known as ital cooking (“ital” is Jamaican patois wordplay on “vital”). Stush in the Bush is a restaurant built on a fifteen-acre farm. Ital cooking is honored here, and dishes are prepared with fresh, local vegetables by a dreadlocked couple, Christopher and Lisa Binns. Expect vegan pizzas topped with plantain, cherry tomatoes, and roasted eggplant; ratatouille served with fresh basil; and tropical greens. The selection of fresh juices—watermelon and lime, ginger and lemongrass—are a necessary addition to counter the flamboyance of the flavorful Scotch Bonnet pepper sauce that accompanies several plates. It’s wise to make a reservation—and don’t come too hungry, because Chris begins every meal with a personal tour of the property. The on-site store sells local preserves, including vegan lemon curd, passion fruit butter, and vegan basil pesto, which make perfect gifts and even better pantry fillers.
Devon House
26 Hope Rd., Kingston
The nineteenth-century home of Jamaica’s first black millionaire is now a National Heritage Site, a house museum, and a center for the best local shopping and desserts. The ground level is inhabited by independently owned specialty stores that celebrate Jamaica’s rich, local flavors through gourmet delicacies. Not to be missed: Devon House Bakery’s selection of beef, chicken, fish, and vegetable patties and the fresh fruit smoothies and coconut water served in its shell from CocoRaw. For your sweet fix, grab a box of truffles made with local cocoa at Chocolate Dreams and try a scoop of tropical ice cream—coconut, guava, and mango are all winners—from the beloved Devon House I-Scream.