It's two twisting, treacherous hours over the Blue Mountains from Kingston to Port Antonio, on Jamaica's wild northeast coast. When you finally roll into town, a few dusty, ramshackle blocks of cinder-block storefronts and jerk-chicken shacks, with gaudily painted rum bars blocking the ocean view and reggae blaring out of cars, you might wonder: Was the drive really worth it?
Port Antonio's first impression is hardly of a Caribbean paradise retreat — there are no sailing clubs, no golf courses, no Margaritaville-style beach bars. Even a sit-down meal can be tough to come by: The only two waterfront restaurants seem to open and close according to when the chef feels like cooking, and if you manage to locate the town's most legendary spot, Dickie's Best-Kept Secret, one local warns, "it could be the best meal of your life or it might be bizarrely awful."
So if your idea of a Jamaican holiday is sipping rum behind the walls of an all-inclusive resort, turn the car around and head for Montego Bay. But if you want to experience a different Jamaica — a rural, slow place that doesn't exist to cater to tourists and operates by its own mysterious rhythms, where a seaside fish joint might turn into a strip joint after sundown, the grocery store sells knockoff Chinese motorcycles, and the best grilled chicken and lobster you've ever tasted are sold on the side of the road and served in a greasy paper bag — you won't find anywhere more magical than Port Antonio.
It's also one of the most serenely beautiful places I've ever seen — the lush Blue Mountains, nestling centuries-old banana plantations, crash into coral-studded ocean coves. Unlike most of the island, which is ringed by volcanic rock, the coastline north of town has a string of perfect beaches: Frenchman's Cove, a tiny crescent where a freshwater lagoon mixes with the warm seawater; Boston Beach, with the island's best surfing waves (and where jerk chicken was invented — don't miss the Boston Jerk Centre); Winnifred Beach, where Rastas sell wood carvings and spearfishermen haul in snapper and lobsters that are cooked in oil-drum grills on the beach.
If you get tired of the beach, head for the mountains. Float down the Rio Grande on the same bamboo rafts that hauled bananas to the harbor 100 years ago. Bomb down jungle trails on a bike. Or soak in the mineral pools at Bath Fountain, discovered by runaway slaves in the 1690s and still basically undeveloped. "Not much has changed in Port Antonio, ever," says Jon Baker, a British music executive turned hotelier who moved here in 2003 and is the man behind Port Antonio's resurgence now. "It's a place stuck in time."
Port Antonio is not so much undiscovered as forgotten. The Caribbean tourist industry was essentially created here in the early 1900s, when "Portie" (as it's known by locals) was the largest exporter of bananas to the United States. Captain Lorenzo Baker of the United Fruit Company got the idea to bring tourists down on his banana boats, and by 1913, 11,000 people a year endured the five-day trip from New York. World War I slowed tourism, and a banana blight in the 1920s killed the export business. Then, in the 1950s, an international airport was built in Montego Bay, and Jamaica's tourism industry moved to the west side of the island, 125 miles away.
Mass tourism never returned to Portie, but in the 1950s, it became a magnet for dropouts and globetrotters, most famously the actor Errol Flynn, who sailed into Port Antonio on his schooner, Zaca, in 1947. (Flynn later bought a 2,000-acre oceanfront cattle ranch, which is still operated by his widow, Patrice, and grandson, Luke.) Over the years, settlers included Prince Sadruddin Aga Khan, LSD-taking British royals Lord and Lady Neidpath (known in the British press as "Lady Mindbender"), and Canadian cookie magnate Garfield Weston, who built the exclusive resort at Frenchman's Cove.
"It was a real club of eccentrics," says Baker, driving his Toyota SUV through the once-chic hillside neighborhood of San San, stopping to point out villas with names like Taipan and Exotique and La Mancha. This area was mostly abandoned in the 1970s, when crime and violence were rampant in Jamaica, and most of the homes have been swallowed up by the jungle, with only a rusting gate or faded sign visible. Still, it's easy to imagine what it must have been like — Malibu or Laurel Canyon in the Caribbean, where Princess Margaret hid out on the private beach at Alligator Head, and Robert Mitchum and Dean Martin drank rum at the Roof Club.
Baker first came to Port Antonio in the 1980s. "I said to myself, 'God, if I'm ever lucky enough, I'd love to buy a place here.' " In 1985, he started a hip-hop label in New York, Gee Street, which released albums by artists like the Jungle Brothers and Stereo MCs. Baker sold the label to Richard Branson in 2000, and, like his former boss, Island Records' Chris Blackwell, he got out of the record business and moved to Jamaica to live here full-time.
Baker built a deluxe recording studio, Geejam, where since 1999 No Doubt, Alicia Keys, Gorillaz, and Amy Winehouse have all cut albums. In 2007, Baker and his partner, Hong Kong–based music executive Steve Beaver, expanded Geejam into a hidden six-acre boutique hotel: six tree house–style rooms overlooking the ocean, with an excellent cove for snorkeling and an open-air restaurant, the Bushbar, where you can feast on sushi and catch house band the Jolly Boys, who've been performing in Portie since the 1940s. After a show at the Bushbar last summer, during which the group covered Iggy Pop and Lou Reed, I asked their nattily dressed, 75-year-old singer, Albert Minott, what keeps the Jolly Boys going. "Keep life simple, be happy," he said. "And drink plenty of overproof rum!"
Baker, who is married to Jamaican singer Nordia Witter, last year opened his second hotel — the Trident, an ultra-luxurious but laid-back midcentury gem, and the adjoining Trident Castle, a 40,000-square-foot re-creation of a 17th-century European manor. (The castle is often rented by bands like Florence and the Machine and Arcade Fire, who recorded there last year.) Baker renovated and manages both properties for owner Michael Lee-Chin, a Toronto-based billionaire who grew up in Port Antonio and is devoted to reviving the economy and tourism industry.
Baker spent nine months meticulously renovating the hotel's 13 spectacular suites, each opening onto oceanfront decks, with dipping pools and outdoor tubs. In the evening, the action takes place at Mike's Supper Club with its Ferrari-red Steinway, featuring live jazz and Jamaican-meets-Japanese cuisine. When I visited, Lee-Chin happened to be vacationing at the Trident, and one evening we talked over drinks by the pool. At 63, he is fit and youthful, dressed tonight in white slacks and high-tops. He tells me his mother worked as a bookkeeper at Frenchman's Cove in the 1960s, and he got his first job on the hotel's landscaping crew at 12. He saved money to go abroad for college, and after earning a civil engineering degree went into business. He spent the next decades building his investment empire, worth an estimated $1.6 billion in 2011. "I'm inspired because Port Antonio has a lot going for it," he says. "The people, the natural beauty, and the history — it's a very special place."
Lee-Chin and Baker's next project is to renovate the restaurant and villas at Blue Lagoon, a 200-foot-deep pool of fresh water and saltwater that is one of Jamaica's most famed landmarks. (Yes, the 1980s Brooke Shields' movie was filmed there, as was the movie Cocktail.) Yet despite the development boom, Port Antonio will likely never compete with easy-access, all-inclusive resort towns such as Montego Bay or Negril. Because unless you're Lee-Chin, who arrived with his party from Kingston in a fleet of helicopters, there's no getting around the fact that it's not easy to get here. Baker doesn't see Portie's distance as a liability. "It's like a natural filter," he says. "It requires a certain type of person to come."
Baker's dream is to turn Port Antonio into a hip, high-end destination, in the way Montauk, at the tip of New York's Long Island, has been remade over the past few years. Artists and musicians have started to buy up the vintage villas near Geejam, and Baker has a plan to renovate the San San neighborhood. "We're creating a new scene here," Baker says. "It's becoming a destination again."
On our last day in Port Antonio, we drive into the John Crow Mountains to Reach Falls. I'd heard that beyond the pristine falls it's possible to hike up the river to a series of caves that runaway slaves used to hide from the British military. There's no clear path, but a lifeguard, Curtis, leads us up a slippery trail, swimming where the path disappears, to a network of narrow tunnels at the source of the river. It's an exhilarating experience to climb through the crevices, then float through silent, subterranean caves. Eventually, the caves connect again to the river, and we swim back down to the falls, leaping 20 feet from the top into a deep aqua pool.
On the way back to town, we stop at Woody's Low Bridge Place, a roadside hamburger stand where, if you call in advance, Woody and his wife, Cherry, will cook up fresh kingfish, lobsters, and steamed callaloo. Tonight we're the only people in the thatched-roof dining area, and Woody, wearing baggy shorts and a Hawaiian shirt, serenades us with a fisherman's tune called "Row Your Boat," which he recorded years ago and sang tonight in a warm, easy tenor.
"The people here have always been really nonchalant, going about their lives with a relaxed generosity and warmth," says Johnny O'Brien, a part-Jamaican, part-American sailing captain and craftsman who works some of the year in Port Antonio. "Montego Bay was probably like that, too — my grandfather described it much the same way as Port Antonio is now back in the early part of the 1900s. But with so many tourists, it became more commercial, tougher, a real us-and-them attitude. Port Antonio is the place where you can feel what Jamaica's really about."
For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!