A handful of resorts and pioneering hoteliers are upping the ante in Jamaica—all over again.

By Bob Morris
November 19, 2012
Credit: Theo Morrison

It’s 11 p.m. on the beach at GoldenEye Hotel & Resort, outside of Ocho Rios, and the Jolly Boys are just hitting their stride. The old-school mento band, fronted by the 74-year-old Albert Minott in a polyester suit and trilby, is delivering hit after hit of calypso-style classics to a large group of casually chic guests dancing in the sand. The fact that few of these guests, here to celebrate a collaboration between the resort and the New York–based Haute Hippie fashion label, were even born when the Jolly Boys first formed in the late 1940’s doesn’t stop them from jumping in and getting down. With a new album, Great Expectation, that features their funky mix of banjo, guitar, and marumba box, the Jolly Boys are enjoying a renaissance these days. They are soulful, scrappy survivors on an island that, much like the band, has been reinventing itself with an eye toward the past.

Hearing the Jolly Boys brings back my own early childhood memories of breezy, sun-filled family vacations on this island 40 years ago. The Jamaica I knew then was one still defined by the cosmopolitan sun-seekers—Errol Flynn, Ian Fleming, Elizabeth Taylor, Richard Burton, and others of their rarefied ilk—who colonized posh pockets of its coastal parishes in the mid 20th century and lent the island a palpable sense of glamour. But since achieving independence in 1962, Jamaica has had its share of growing pains. An alliance with Cuba during the Cold War took it off a short list of chic places for the American elite—who had been coming in droves. Headlines about poverty, unrest, and violence in the decades that followed ruled it out as an easy Caribbean destination, too, despite the popularity of Bob Marley and Jimmy Cliff. Homophobic incidents and laws didn’t help. Neither did cruise-ship overload and all-inclusive overkill, phenomena that might have improved the sputtering economy, but did nothing for the reputation of the island among the sophisticated set.

But lately, a stylish crowd has been discovering Jamaica all over again, encouraged by a handful of iconoclastic resort owners. Rather than sequestering guests behind closed gates, this new breed of hotelier is tapping in to what makes the island so special beyond its beaches and weather—its complex topography, rich history, and vivid culture.

“It’s sometimes a fight getting guests over their negative perceptions,” says the informal yet formidable Chris Blackwell, whose Island Outpost hotel brand includes GoldenEye; Strawberry Hill, in the Blue Mountains above Kingston; the Caves, poised on cliffs in west Negril; and Port Antonio’s Geejam. “But the island is full of bright, talented, and funny people who love being Jamaican. They are the greatest asset of this country.”

Blackwell should know. Born in London but raised in Jamaica, the Rock & Roll Hall of Fame inductee and Island Records founder produced Bob Marley, Toots and the Maytals, and a roster of non-Jamaican musicians including Cat Stevens, Roxy Music, U2, Tom Waits, and others. In the early 1990’s, he branched out into the hotel business, opening properties in Miami at the beginning of its revival. (His hotels played a major role in resurrecting the city’s Art Deco District.) He did the same thing in Jamaica on a grander scale in the mid 1990’s, as Island Outpost took the laid-back cool of reggae style and applied it to resorts. GoldenEye is a collection of 21 villas, suites, and cottages spread across 52 coastal acres. At its heart is Ian Fleming’s original three-bedroom villa, where the author wrote all 14 of his James Bond books. The resort emerged from a top-to-bottom renovation and expansion two years ago that added some serious polish to the place without diminishing any of its Jamaica-influenced personality.

“The main thing for me is to attract guests who are imaginative and curious about life,” Blackwell tells me over a glass of coconut water on the patio of the secluded tree-house-like cottage on GoldenEye’s lagoon, where he stays when visiting the resort. “I like to create places where people can explore the area, then come back to the bar and talk.”

Indeed, with a fleet of WaveRunners, boats, cars, and kayaks at the ready, guests can visit the nearby town of Oracabessa; Ocho Rios, with its blossoming local art scene; Noël Coward’s Modernist-style retreat, Firefly; and James Bond Beach, a popular weekend gathering spot for fishermen and their families. And with the road to Port Antonio paved not all that long ago, guests can also finally drive to the eastern side of Jamaica in less than two hours.

Hemmed in by the Blue Mountains on one side and the Caribbean Sea on the other, Port Antonio lured everyone from J. P. Morgan and William Randolph Hearst at the turn of the 20th century to Princess Margaret and Errol Flynn in the 1950’s. Then, after decades off the radar, Geejam came along. The tiny and luxurious colony of villas with a world-class recording studio opened in 2007 and rebooted the area for hip travelers.

Jon Baker, the producer behind the Jolly Boys and Geejam’s co-owner, is a visionary and champion of the island in the Blackwell mold. He fell in love with Port Antonio when visiting in the 1980’s and was inspired to build a studio there in the mid 1990’s. It became so popular with musicians that Baker ended up creating a small resort to house them and other guests.

With just five accommodations and the Bush Bar open-air restaurant, Geejam doesn’t offer guests much in the way of on-site activities beyond a pool table and fitness room (and recording studio, of course). As an early guest there (staying in a villa with artwork by the infamous graffiti artist Banksy), I was encouraged to walk down to the sweet little village of Drapers and then make my way over to the beach at Frenchman’s Cove Resort, a onetime jet-set destination now popular with locals who eat snapper and salt fish at the hotel’s authentic shack of a restaurant.

We met welcoming people everywhere, both native Jamaicans and foreign homeowners like Patricia Wymore Flynn, the cattle-ranching widow of Errol, and the art collector Francesca von Habsburg-Lothringen, who invited us and other Geejam guests to her raucous New Year’s Eve bash. But the best part of the visit was a trip to the Rio Grande, an hour’s drive into the interior, where boatmen poled us on bamboo rafts festooned with flowers along the crystalline blue river. It was a serene experience that removed us from all thoughts of the modern world. Years ago this was the way bananas got to market, and it inspired the folk song that Harry Belafonte later made famous as “Day-O (Banana Boat Song),” as well as Errol Flynn’s legendary rafting parties.

Baker, British-born, but now also a Jamaican citizen, sees this entire area, with its untouched swaths of tropical mountain beauty (lagoons, rain forests, mineral baths, and waterfalls) as an underutilized paradise. He’s currently renovating two properties, set to open this winter, just outside Port Antonio—Trident Hotel, a series of luxurious waterfront villas that date from the 1960’s, and the magnificent white Trident Castle, built nearby in the 1980’s by an eccentric island architect. Baker has also taken over the dockside restaurant at the Blue Lagoon, a 15-minute drive from Port Antonio, and plans to reopen it as a casual lunch joint that doubles as a romantic dinner spot. Next door, he’s planning a spa with a freshwater bathing spring beside it. Meanwhile, he’s intent on promoting the Errol Flynn Marina, in Port Antonio, as a yachting destination. It’s a big to-do list. “Sometimes I feel like Fitzcarraldo,” he tells me as we make our way past the Blue Lagoon’s hanging moss to the dilapidated, cavelike site of his imagined spa. “But my goal is to make this area more accessible to tourists and Jamaicans alike.”

What started as a tentative dip into hotels for him has blossomed into a renaissance for the entire area—if not the island. “There’s a new positivity in Jamaica with a new government,” he says of the fresh approach taken by the recently elected prime minister, Portia Simpson Miller of the People’s National Party, that includes speaking up for more education and social programs and against deep-seated homophobia. “And I’ve seen an upsurge in pride.”

He’s talking about what Novia McDonald-Whyte, a lifestyle editor at the Jamaica Observer, calls Brand Jamaica, something beyond beaches, reggae, and jerk chicken. “There are so many ways Jamaica pulls above its weight with its history, nature, culture, and resorts,” says McDonald-Whyte, who has a penchant for wearing big white-framed eyeglasses and the best Jamaican designers. “Visitors don’t just want the sun,” she says. “They come here because this is home to runners such as Usain Bolt, or to raft down the most beautiful river in the Caribbean, the Rio Grande.”

They can also now come to Jamaica for locally sourced meals that would have been unheard of just 10 years ago, when island food was lackluster at best. Everywhere from the elegant, traditional Jamaica Inn, in Ocho Rios, to Jakes Hotel, a low-key resort of 27 eclectic cottages and two villas on the remote southwestern coast, I found chefs working with farmers and fishermen to uplift their menus. Jakes offers farm-to-table dinners, served on site at area farms. There’s even a community-supported agriculture business, Potosi Farms, which delivers sustainable produce to hotels, restaurants, and homeowners island-wide.

Of course, some visitors still want what they always wanted from Jamaica, a quick flight to good weather in winter and an elegant experience on the sea. For this they can turn to Round Hill Hotel & Villas, a favorite of the socially prominent for 60 years, including Grace Kelly and Babe and Bill Paley, who owned grand “cottages” along the hills above the resort’s beach. Today, the 110-acre resort on its own peninsula has 27 villas and 36 hotel rooms recently redesigned in classic tropical style by Ralph Lauren (a property owner on Round Hill’s board).

“The social history here is fascinating,” says Josef Forstmayr, Round Hill’s affable managing director, over a dinner of Jamaican rock shrimp and pole beans with fresh mint (from the resort’s own organic garden) at the Grill, an open-air seaside restaurant on a sprawling terrace. He rattles off a list of royals and iconic figures who have visited the resort and tells me that my own imposing cottage, No. 25, once housed John and Jackie Kennedy. What’s even more exciting is the fact that Ryan Gosling, one of many younger celebrities flocking to Jamaica these days, stayed here last winter. Rather than stick around the property, he got out on a motorcycle to explore, taking in concerts at clubs and a major street party in Kingston. “And when Paul McCartney comes,” continues the puckish, Austrian-born Forstmayr, “he sails a Sunfish over to the dock and shoots the breeze with everyone. They know who he is but don’t make a fuss. Jamaicans will talk to anyone.”

Devoted as Forstmayr is to his world-famous clientele, who treat him as much like a friend as a manager, he’s more devoted to the island itself, with all its twists and bumps. “If you want everything smooth, you can go to St. Bart’s,” he says. “This island is about real life.”

Jason Henzell is yet another hotelier who understands that. As the owner of Jakes, in the town of Treasure Beach, he has become so integrated with the community that he might as well be mayor. His mother, Sally, designed the cluster of modest little cottages in 1991. Since then, it has developed into a popular spot for travelers in search of authenticity—thanks, in large part, to Henzell’s extraordinary commitment to the Jamaican community around him. When I visited there last Christmas, he encouraged us to get to know the area and even joined us on a boat ride to Black River, a town of fishermen and port workers. As we zipped along the waters of Treasure Beach, a scrappy and happy little village where Henzell has many development projects under way, he sighed.

“There’s so much to do around here,” he said. “But it will get done through community and visitor engagement.” At the time, he was getting ready to open a sports camp for 1,200 area kids funded by grants and devoted guests who support his efforts. He regularly hosts the Calabash Literary Festival, and he continues, through the local service organization he heads, to pull in funding for health care, a fish sanctuary, and agricultural projects, which include his enterprising farm-to-table dinners.

Not far from him, in Negril, the Rockhouse Hotel, a cluster of cliffside bungalows that attracts a bohemian set, has also taken community engagement to a new level. In 2008, its foundation funded a major library renovation. And last winter, in Little Bay, a small fishing village a half-hour from Negril, the foundation completed a makeover of a grammar school. (These efforts, incidentally, earned the Rockhouse a Travel + Leisure 2012 Global Vision Award.) The hotel offers guests the chance to visit the library and school every Thursday.

“Visitors want to know there’s a fuller impact of their travel dollar here,” Peter Rose, the foundation’s president, tells me as we drive past fishing boats and coconut palms to see the school. “It makes people feel good to see the real Jamaica.” Indeed, I’m impressed to find a polished two-story school that was, until recently, decrepit and inadequate. The students look inspired. “They’re passionate about education, they really want to learn,” one teacher tells me.

I step into a classroom where all eyes are upon me. “Good afternoon, Mr. Morris,” they say in unison. “Welcome to the Little Bay All Age School. We hope you enjoy your visit.”

I do, very much.

Getting There

Most major airlines have direct flights into Kingston or Montego Bay. The majority of the island’s resorts are within a two- to three-hour drive of either airport. Charter flights to local airstrips are also available.

Getting Around

You can rent a car in either Kingston or Montego Bay; improved infrastructure has made exploring the island much easier. If you prefer not to drive, arrange transfers with your hotel.


The Caves Thirteen cliffside suites and cottages, just outside of Negril. Negril; islandoutpost.com. $$$

Firefly Beach Cottages Beachside resort of affordable cottages. Negril; jamaicalink.com. $

Geejam Port Antonio; geejamhotel.com. $$$$

Jakes Hotel Treasure Beach; jakeshotel.com. $

Jamaica Inn Old-school resort of suites and cottages on a quiet, private beach. Ocho Rios; jamaicainn.com. $$$$

Strawberry Hill Hotel Spa & Gardens Secluded resort of historic 19th-century cottages perched high in the Blue Mountains. Irish Town; islandoutpost.com. $$$

Trident Castle Opening winter 2012. Port Antonio; geejamcollection.com. $$

Trident Hotel Opening winter 2012. Port Antonio; geejamcollection.com. $$$$$

Tryall Club Private golf and tennis club with 79 villas for rent, each with a chef and housekeepers. Montego Bay; tryallclub.com. $$$$


Frenchman’s Cove One of the country’s most pristine beach communities, with a network of lush nature walks. The popular seaside restaurant at the Frenchman’s Cove Resort serves authentic Jamaican snacks. frenchmanscove.com.

James Bond Beach Great for celeb-spotting and mingling with locals. Time your visit to coincide with one of the many concerts that take place on the lawns just off the beach. Oracabessa.

Rio Grande Hire a guide for a rafting tour down one of Jamaica’s largest rivers with striking views of the nearby banana groves and the Blue Mountains just beyond. explorejamaica.com.jm.

Hotel Pricing Key

$ Less than $200
$$ $200 to $350
$$$ $350 to $500
$$$$ $500 to $1,000
$$$$$ More than $1,000

Strawberry Hill Hotel Spa & Gardens

Tucked high in the Blue Mountains with drop-dead views of the far-off Caribbean and Kingston, Strawberry Hill is a luxurious oasis of tranquillity that’s light-years removed from raucous coastal Jamaica. Shrouded in morning mist and thick tropical forest, the 13 Georgian-style cottages evoke British colonial days. Décor runs heavy on antiques and 19th-century period reproductions, including mahogany four-poster beds draped in gauzy fabric, and some rooms have balconies that hang off the mountainside. But this brainchild of Jamaican record impresario Chris Blackwell (whose family has owned the property, a former fruit plantation, for decades) isn’t all peace and mountaintop serenity: the rooms are equipped with cutting-edge sound systems and CD libraries.

Jake's Hotel

An utterly funky hotel overlooking Treasure Beach on the secluded south coast, Jake’s lives and breathes eccentric, from the free-form swimming pool to the multiculti, hippie-chic décor. The 43 bungalows—many of them right on the beach or set atop rock outcrops that overlook the sea—were created by local theatrical designer Sally Henzell in the early 1990’s, and they’re still unlike anything else in Jamaica. Two notable restaurants serve gourmet Jamaican food like pumpkin and ginger soup, jerk chicken, and just-caught lobster from local fishing villages.

The Caves

Located atop Negril’s limestone cliffs, the Caves is an all-inclusive, adults-only resort surrounded by 10 acres of tropical gardens. The resort seems to rise organically from the cliffs, with curved-stone walls and stairways leading down to the water. The 12 thatched-roof cottages are built of wood and stone, and each is individually decorated with bright pastels, island-style fabrics, handcrafted wicker furniture, and large windows that open onto views of the Caribbean. The bar, spa, and saltwater pool overlook the sea, and a candlelit cave is available for private dining. Water activities include cliff diving, snorkeling, and kayaking.

Round Hill Hotel & Villas

A west shore institution, Round Hill is one of the places that put Jamaican tourism on the map. Over the years, many a famous name has slept here, from presidents and prime ministers to movie stars and professional athletes. The 36 white-on-white rooms are spread between the two-story Pineapple House overlooking the infinity pool and beach, and 27 private villas (most with their own pools) scattered among the property’s coconut, pineapple, and allspice groves. The 18th-century great house is now a luxury spa, the cocktail lounge and piano bar were designed by Ralph Lauren, and culinary maestro Martin Maginley oversees one of the best resort kitchens on the island.

Jamaica Inn

Gracing its own sandy cove on the east side of Ocho Rios, this classic Caribbean resort has been around since the colonial days of the 1950’s. It has long been a favorite among visiting British elite, including the likes of Winston Churchill. Thoroughly spruced up in 2007, the 47 suites are a blend of Indonesian, colonial, and retro Jamaican décor, but remain refreshingly unplugged, with no TV’s to shatter the peace. Every suite has its own outdoor space, with a private infinity pool and sea entrance just steps from the bedrooms. Although the Jamaica Inn offers the usual distractions like couples’ massages at the KiYara spa, it still cultivates a colonial air, with croquet on one of the sweeping lawns and polo lessons at nearby Chukka Cove equestrian center.

Rockhouse Hotel

This ultrahip hangout takes its name from its cluster of thatched-roof bungalows built atop rock cliffs that jut just above an aquamarine cove. Most of the 34 so-called rock houses are outfitted with private patios or sundecks; a few have private ladders leading right down into the sea. With four-poster beds made of local timber and covered in the softest linens, soaring ceilings, and giant windows facing the sea or gardens, the rooms encourage ordering breakfast in bed before venturing out for snorkeling in the sheltered waters of the reef or an “On the Rocks” massage (ask for Joy or Maureen) in the new open-air, cliff-top spa. Your dollars do double duty; your vacation helps build and repair local schools and expand libraries. Since 2004, the Rockhouse Foundation has donated over $500,000 to its community.

GoldenEye Hotel & Resort

Jet-set bohemians and creative types have flocked to GoldenEye since the mid 20th century, when it was the cliff-top retreat of Ian Fleming, who wrote 14 of his James Bond novels here. Fresh from a two-year overhaul completed in 2010 courtesy of its current owner, Island Records founder Chris Blackwell, the property has morphed from private villa rental to full-fledged 22-room hotel. But thanks to Blackwell’s irrepressible, highly personal touch, the mood remains the same: a tropical playground for well-traveled expats from some latter-day Noël Coward play. Amid gardens of banyan and mango trees, the new waterfront cottages have ultramodern amenities (kitchen appliances by Renzo Piano) and design flourishes from Blackwell’s stylish friends (including Barbara Hulanicki of Biba and Pink Sands fame). Fleming’s original three-bedroom villa is available for booking and still features the writer’s own desk, carved out of Jamaican red bulletwood and surrounded by louvered windows looking out to the sea.

Geejam, A Private Hotel

Until recently, former music execs Jon Baker and Steve Beaver rented out Geejam, their lush 46-acre estate in the hills off Jamaica’s northeastern coast, to musicians like Gwen Stefani and India.Arie to use as a recording studio. Since the two teamed up with Island Outpost, the seven-room retreat is now open to anyone looking to channel their inner Lenny Kravitz—which is easy enough to do thanks to the hotel’s rock-star–cool design (think Juergen Teller prints and Philippe Starck chairs). Guests can even lay down a few tracks of their own at the on-site studio.

The Tryall Club

Located on a former sugar plantation near Montego Bay, the 2,200-acre Tryall Club is one of the most spacious resorts on the island. Bordered by the Caribbean Sea on one side and rolling hills on the other, the property includes 86 private villas, a working 18th-century water wheel, and a renowned championship golf course. The one- to eight-bedroom villas, some of which are located in the 1834 Georgian Great House, all include a personal staff, private pool, and views of the sea and golf course. The resort also has three bars and three restaurants, including the fine-dining Great House Restaurant.