• Introduction
• Nevis
• Kamalame Cay, Bahamas
• Jamaica

Jamaica

Beyond the tourist compounds, these four boutique retreats offer real local flavor in the lap of luxury

Jamaica is a pioneer of all-inclusive holidays with plentiful rum, Red Stripe beer, and reggae within gated resorts that feature predictable tropical touches. While that breed of worry-free vacation has its appeal, we also love the other, relatively under-the-radar side of Jamaica, beyond the tourist centers of Negril, Ocho Rios, and Montego Bay. With Jamaica’s checkered history, it’s natural to wonder if going off the path is advisable. The answer is yes, but it’s not always easy to do so in an ad hoc way. The four rare and wonderful boutique hotels we’ve found aim to provide a more peaceful, laid-back experience that embraces the island’s supervibrant, diverse population (from dance-hall stars to cricket enthusiasts, for starters) rather than cordoning it off. They also draw on the strength of Jamaica’s famed local food (think fried ackee and jerk chicken) and provide access to some of the more remote—and worthwhile—attractions, like undisturbed beaches and villages. All the while, high-end perks, like organic spas and fireside bars, prevail at these amazing retreats.

Three of our picks are from the Island Outpost group, founded by Chris Blackwell, a legendary music producer who grew up on Jamaica and is now committed to creating hotels that achieve the difficult mix of superb service with zero pretense. All four places provide the full scope of Jamaican landscapes and culture in a relaxed, safe environment where guests are likely to be discerning travelers.

Blackwell, who started Island Records and is known for popularizing Bob Marley worldwide, has done much to promote the low-density, individualistic approach to tourism on Jamaica. Strawberry Hill Resort, Jake’s Resort, and Geejam Hotel—three of the properties in his Island Outpost hotel group—provide a slice of Jamaican life, with intimate vibes reminiscent of staying at a friend’s home.

Nestled high in the Blue Mountains, which rise from the northern edge of Kingston, Strawberry Hill began as an 18th-century coffee plantation deeded by the British royal family to Horace Walpole, the renowned novelist and earl. Acquired by Blackwell in 1972, it has since developed a reputation as a place to go for rest and relaxation; it’s known for an emphasis on healthy living and a stellar spa (Strawberry Hill Living) that specializes in Ayurvedic healing. Bob Marley recovered here after being shot in 1976; recent guests include Bono, Kate Moss, and Prince Charles. It’s situated on 48 acres and surrounded by a lush coffee plantation (don’t miss the Blue Mountain brew) and botanical gardens with 350 species of plants and flowers. The resort fosters an environment in which it’s easy to feel a sense of rejuvenation.

The 12 airy Georgian-style cottages feature details such as four-poster beds, hand-carved fretwork, and louvered windows. A 60-foot negative-edge pool highlights a stunning panorama of Kingston below. This mountaintop oasis also encompasses an acclaimed restaurant that serves nouvelle Jamaican cuisine and has a cozy fireside bar (nights can get chilly). Guided tour options include bird watching, mountain biking, and visits to coffee estates and nature trails around the Blue and John Crow Mountains National Park.

On the island’s rather remote southern coast, in low-key Treasure Beach, is Jake’s, the chic former holiday home of Sally Henzell, Jamaica’s foremost decorator, and her husband, Perry, director of the iconic Jamaican movie The Harder They Come. Named for the family’s pet parrot, this bohemian hideaway—today run by their son, Jason—has 23 secluded cottages, two restaurants, a holistic spa, and a saltwater pool. Jake’s is Jamaica at its most prototypical: rootsy, funky, and community-focused. The embodiment of the close-knit vibe is Breds, a nonprofit association cofounded by Jason that helps develop and fund a variety of local projects, such as installing GPS systems for fishermen. Fun activities are available in the immediate surroundings, including tours of roadside bars and a visit to Pelican Bar, perched on stilts smack in the middle of the sea. Other excursions include boat tours to spot crocodiles on the Black River; an outing to the spectacular YS Falls; and a ride along leafy Bamboo Avenue, a canopied road lined with vendors selling deliciously sweet coconut and peanut treats.    

In the heart of the Jamaican bush on the island’s northeast coast, Geejam Hotel, the newest Island Outpost property, started life as a recording studio for the likes of Björk, No Doubt and Gwen Stefani, and Gorillaz. Music is still in its blood. Three musically named cabins—Ska, Mento, and Rocksteady—come with unique touches like steam rooms and verandas with Jacuzzis; there’s also a fabulous suite and a three-bedroom villa. It may be tempting not to leave the premises: The seven units, with Philippe Starck furniture and cutting-edge amenities like Apple iTVs, provide the ultimate in organic elegance. Geejam draws all manner of celebrities: Sharon Stone celebrated her 50th birthday here; Grace Jones raved about her stay. Recording packages are available for guests, so you too can book time on the mike in the state-of-the-art music studio. The Bushbar restaurant, framed by a pair of ancient fig trees, is known for its unusual Jamaican-Japanese fusion dishes. In the surrounding area—Jamaica’s most pristine—you can visit Port Antonio, once home to Ian Fleming and a prime tourist spot. It’s now a laid-back hub with a hopping central market and a charming boardwalk. Also nearby are some of the island’s best beaches and the Rio Grande, known for its fantastic rafting.

Jamaica Inn—an old-school luxury retreat run by the Morrow family since 1958—is more of a white-glove experience compared with the Island Outpost resorts, but it still provides an intimate holiday beyond the gated compounds. During the inn’s heyday, Winston Churchill painted in the garden, and Noël Coward and Errol Flynn paid regular visits. Now the retro ambience, highly experienced service—one staff member, Teddy, has worked there for 50 years!—and timeless style are cherished by repeat visitors. The property, on a private cove in Ocho Rios (lovingly called “Ochee” by the locals), boasts 47 spacious suites and four two-bedroom cottages, all with a private balcony or a veranda. The inn’s alfresco restaurant gets top marks for flavorful local cuisine, and the seaside spa offers holistic treatments. The north coast around Ocho Rios offers prime excursions, such as tours of nearby historic estates, including Prospect Plantation, Firefly, and Harmony Hall. Many of them have been restored and are now open to the public as museums, offering a glimpse of Jamaican island life as it once was.

MAKING IT HAPPEN

GETTING THERE
Fly into Norman Manley Airport in Kingston or Donald Sangster International Airport in Montego Bay. Air Jamaica flies nonstop to both from New York and Miami. American Airlines flies nonstop to both from Miami, nonstop to Montego Bay from New York, and direct to Kingston from New York. JetBlue joins in with nonstop service from New York to Montego Bay starting in May. Strawberry Hill and Geejam are closest to Kingston, while Jake’s and Jamaica Inn are closer to Montego Bay. Each hotel will arrange for airport transfers, while Geejam and Jamaica Inn can arrange special air transfers to nearby airstrips.

WHERE TO STAY
Sherman's Picks
* = Smart Splurge
+ = Great Value

* Geejam Hotel Port Antonio; from $495/night starting April 20, including breakfast and free airport transfer with minimum 4-night stay; 800/688-7678, 876/993-7000, geejamhotel.com
* Strawberry Hill Irish Town, St. Andrew; from $495/night starting April 20; 876/944-8400, strawberryhillresort.com
+ Jake’s Calabash Bay, Treasure Beach, St. Elizabeth; from $95/night starting April 20; 876/965-3000, 876/965-0635, jakeshotel.com
Jamaica Inn Ocho Rios, St. Ann; from $300/night starting April 16; 800/837-4608, 876/974-2514, jamaicainn.com

WHERE TO EAT AND DRINK
Pelican Bar Head out by boat to this hut built on a shoal three-quarters of a mile offshore for mellow times, cold Red Stripe, and fresh seafood on request. Boats arranged through Jake’s.
Strawberry Hill With a number of dining areas and some of the best cuisine on the entire island, the resort’s own kitchens are a delight.
Mille Fleurs Close by Geejam is one of our favorite eateries in all of Jamaica. Enjoy classic fine cuisine made from local bounty (At Hotel Mocking Bird Hill, Port Antonio; $60 tasting menu; 876/993-7134, hotelmockingbirdhill.com).
Evita’s Just down the road from the Jamaica Inn, Italian tradition meets Rastafarian cuisine in creations like lasagna with ackee and calaloo (Eden Bower Rd., Ocho Rios, St. Ann; entrées from $18; 876/974-2333, evitasjamaica.com).

WHAT TO DO
Jake’s The hotel will arrange a tour to the mouth of the Black River, a unique seaside environment with mangrove swamps and wetlands full of animals including dolphins, rare birds, and crocodiles. A bit farther afield, 120-foot YS Falls is a great attraction, whether you’re swimming, tubing, or just admiring.
Strawberry Hill The resort has a number of great spa services, while the surrounding areas provide outstanding hiking, biking, and birding opportunities.
Geejam Divers head to the Errol Flynn marina, rafters to the Rio Grande River, and many enjoy the town, a walk on the boardwalk, the fresh fish restaurants on Folly Road, or the shops on Market and Harbour streets.
Jamaica Inn The inn can arrange any number of outings, including polo matches on Saturday afternoons, as well as horseback riding all week and mountain biking in the St. Ann Mountains. There are several golf courses nearby, and don’t miss a visit to Noël Coward’s house museum in Port Maria.

WHEN TO GO
During the winter, hordes of travelers (including spring breakers) come to Jamaica. From mid-April through May, and again in fall, travelers benefit from reduced rates on air and hotel packages (except during the Easter holiday), less crowded beaches, and cheaper green fees. Weather can be rainy from June through November.

See Bahamas Travel Guide | See Jamaica Travel GuideSee Nevis Travel Guide