Where to Eat, Drink, Stay and Play in Jamaica

Channel your inner James Bond at the Fleming Villa, or marvel at secluded waterfalls while taking a private tasting of the region’s renowned coffee atop the magnificent Blue Mountains.

Aerial view of the storied Fleming Villa, GoldenEye, Oracabessa Bay. 

From the moment Ursula Andress struck one of the world’s most iconic female silhouettes, strolling sensuously from the surf in 1962’s Dr. No, there’s been an undeniable chemistry between James Bond and Jamaica. Turns out the sultry relationship is back on simmer in the latest in the 25-film franchise, No Time to Die, which like the original takes place partly in the Caribbean island nation. 

Stylish interiors enhance GoldenEye’s welcoming reception.

According to Forbes, cast and crew gathered at Ian Fleming’s GoldenEye estate-turned-resort to kick off production of Bond 25, with many remaining to film scenes on the island. Daniel Craig’s fifth and final Bond outing will be released this April. For a film franchise that increasingly enjoys self-referential nods to its own canon, it’s no surprise they found a way to return to the idyllic island. 

Sip and suds the day away in the Fleming Villa’s lime green alfresco bathtub.

Declassified just in time for winter escape planning, an exclusive partnership between global private jet firm VistaJet and Jamaica’s iconic hotel brand Island Outpost gives you unparalleled entree to the luxurious side of James Bond’s literary birthplace. The VistaJet fleet, which includes the $20 million-plus Bombardier Challenger 350, is cleared to access the Ian Fleming International Airport, about 10 minutes from GoldenEye on Jamaica’s north east coast. 

GoldenEye is a playground for Bond junkies.

Though labeled an “international” airport, it’s really more of a high-security small-scale executive airfield, a rarity in the Caribbean, and rather apt for an aviation hub named after the Bond creator. Fleming’s GoldenEye on Oracabessa Bay is the island’s most coveted 007 address. The British naval intelligence officer-turned-author purchased 15 acres of tropical underbrush, formerly a donkey racetrack, in 1946, and set about building his dream villa. 

Fast forward to 1976, when Island Records founder Chris Blackwell acquired the property to entertain friends like Sting, who wrote the chart-topping “Every Breath You Take” while on a tropical escape here. Over a period of 30 years, Blackwell, who signed U2 to its first record contract and launched legends such as Bob Marley, Cat Stevens, and Roxy Music, added 25 acres to the original parcel, peppering cottages into the mix of villas and launching a second career as a hotelier in the process. 

Setting sail at sunrise on a sleek yacht in Port Royal, photographed by Corey Hamilton (@coreymus).

Bond aficionados on the VistaJet junket, starting at $23,000 per person (based on double occupancy) can check into the Fleming Villa, GoldenEye’s original residence, complete with a private beach, private pool and tropical gardens. This highly-desirable retreat features the author’s personal items, including the very desk at which he wrote all of the 007 novels. It doesn’t get much more fetishistically Fleming-esque than this. Emerge at your leisure to enjoy sunset cocktails at playwright Noël Coward’s nearby residence. Take a dip in the Blue Lagoon, raft down the tranquil Rio Grande; your wish, your whimsy. 

Farm-to-table dining at Pantrepant.

VistaJet guests can also enjoy a takeover of Pantrepant, a nearby farm owned by Blackwell, to revel in scenic horseback rides before returning for farm-to-table dining. And your bespoke Bond journey could include private snorkeling trips and dancing to a live reggae band at The Caves hotel in Negril, home to the Blackwell Rum Bar hidden in a cliff just like a Bond villain’s lair. 

Bond aficionados are drawn to sunset cocktails at Blackwell Rum Bar, The Caves.

Repeat visitors to Jamaica know the real deal. Sure, the island’s sensuous shorelines may be the initial draw, but to truly relish in the national flavor and feel, head for the hills. Another of Blackwell’s posh properties, Strawberry Hill, sits 3,000 feet atop the magnificent Blue Mountains; think secluded waterfalls and private tastings of the region’s renowned coffee. He bought the historic estate, back in 1972, entertaining guests like The Rolling Stones, Marianne Faithfull, and Willie Nelson, and in 1991 transformed it into an intimate 12-cottage hotel and spa. 

Strawberry Hill sits 3,000 feet atop the spellbinding Blue Mountains.

Strawberry Hill was once a popular place for international and domestic artists to record, as seen in photographs of Mick Jagger and Peter Tosh, now hanging with pride of place in the bar. Home to a significant photographic tour of music’s most illustrious players, rock and reggae junkies who book the conference room can also revel in the wall-to-wall platinum records on display. 

A serene setting at Rockhouse Hotel & Spa in Negril.

Blackwell leans into Strawberry Hill’s laidback lifestyle with aplomb, sometimes indulging in three-hour lunches on the terrace. We shared such a lunch the week of Prince Harry’s visit to Jamaica in 2012 (think Scotland Yard on speedboats). Reporting on the young royal’s first solo royal tour revealed Jamaica’s finest hour; we watched him dance to reggae at a youth center on a visit with Rita Marley, “sprint” against Usain Bolt, and party on a private island in Montego Bay. 

Rick’s Café features live reggae, cliff diving and seriously sublime sunsets.

Dubbed one of the coolest watering holes in the world, Floyd’s Pelican Bar is a quirky driftwood shack on stilts on a sandbar about a mile out to sea in Parottee Bay. Reachable only by boat, preferably a yacht tender, it makes for a fun haute-to-hut spot for your charter vessel. When the nightlife mood strikes, hit Rick’s Café on the West End cliffs of Negril. 

This hotspot boasts seriously sublime sunsets, live reggae, and cliff diving. The highest platform is 35 feet and features local divers performing acrobatic stunt dives; gutsy patrons chase their Campari cocktails with heart-throbbing cliff jumps into the sea. The main stage hosts local and international bands while Rick’s After Dark offers an upscale lounge experience. 

Perched on the rugged cliffs of Negril, Tensing Pen Resort is renown for rustic charm and romance. 

Laying down slick tracks more appealing than rum-soaked sunbathing? With its genesis as a music studio, Geejam was born cool as it evolved into a small hotel featuring recording facilities. According to Harper’s Bazaar, when Banksy checked in, creative vibes hit big and he ended up making a piece for the hotel to keep. When Beyoncé and Jay-Z came to stay, the place hit peak payload. 

A hushed haven, we’re not surprised the reigning hip hop royals chose this plum spot to share plantain chips in peace. Featuring three luxury villas and four cabins tucked into the lush rainforest of Port Antonio, the hotel has hosted Rihanna, Florence Welch, and Sharon Stone’s 50th birthday bash. With 12 new rooms aimed at a younger clientele, there’s never been a better time to channel your inner Harry Styles. After all, the Brit boy wonder rocked out at Geejam as a base camp to record his debut solo album. 

Rose Hall Villas at Half Moon epitomize gracious living. 

More game for golf and gastro hedonism? Find your happy place at Half Moon. Unraveling across a constellation of coves and hypnotic water features, Half Moon is a golfer’s dream. Designed by Robert Trent Jones, Sr. in 1962, the resort’s course was later modernized by Roger Rulewich, who removed non-native trees, expanded greens, and renovated bunkers, creating a juggernaut of inventive challenges. After 18 holes, savor the resort’s signature restaurant, Sugar Mill. Set within an elegantly restored sugarcane mill, Jamaican-born chef de cuisine Christopher Golding crafts island food journeys from farmland to fishing bay. 

The Tryall Club, an exclusive Caribbean country club resort, spread out over 2,200 lush acres.

Crispy jerk chicken rolls with cho cho slaw and sorrel-dark rum chutney are addictive, while coconut-crusted grouper fillet and steamed cassava bammy had us at hello. And the new $75 million expansion Eclipse at Half Moon, one of the most opulent additions to the island in a generation. The eagerly-awaited enclave features 57 new accommodations, an infinity-edge pool, a natural swimming cove, and a remarkable array of seven bars and restaurants where foodies can forage. 

Entrepreneur/businesswoman Tia L.D Johnson (@lovetia.xo) at Shaw Park Beach in Ocho Rios. “Oftentimes we take these [natural] treasures within our grasp for granted. With the drastic shift in our lives and daily normalcies, it’s humbling to revel in the discovery of Jamaica’s abundant hidden gems. Our food, our people, our music, our dialect and candor, our lifestyle and overall culture are what makes it all so uniquely special. We are magic and Jamaica is paradise!”

To a winter-weary traveler, nothing soothes sun-starved eyes quite like the robust aura of Round Hill Hotel and Villas. When hunting for a whole villa takeover for family and friends, the legendary resort presents a rather impressive inventory. A throwback to old school Caribbean charms, this is where celebrities chase a bit of anonymity, peeling off Chanel cashmere on arrival in warmer climes. The resort was originally conceived by Jamaican-born entrepreneur John Pringle, who invited prominent American and European socialites to build private villas on his 110-acre peninsula, once part of Lord Monson’s plantation in Montego Bay. 

Round Hill’s Pineapple House offers 36 oceanfront guest rooms artfully designed by Ralph Lauren. 

Debuting in 1953, Round Hill’s poetic homage to the idyllic north coast proved irresistible, rising as the private haunt of style icons like Ralph Lauren, Oscar Hammerstein, and Bill and Babe Paley. Many villas remain owned by the next generation of the original families, all of which are available to guests when owners are not in residence. 

Trident Hotel’s dramatic infinity pool offers guests sweeping ocean views.

Comprised of 27 private villas nestled into the hillside of tropical gardens, the resort’s Pineapple House offers an additional 36 oceanfront guest rooms artfully designed by Ralph Lauren. Each precious day here tumbles spiritedly into the next, little perks pile on bigger perks; a delicious dash into the sea, sunset cocktails on your sprawling private terrace. Catering to romantic overtures, this is a cufflinks and kitten heels kind of place—where a magnum of Moët & Chandon is always on ice.