FOR MANY YEARS, Port Antonio, a junglehemmed town on Jamaica’s northeast coast, was synonymous with a specific kind of languorous glamour, best illustrated by a 1955 photograph of Patrice Flynn, a movie actress and wife of Errol. In it, she is riding on horseback along a sandy track as he walks beside her, his white shirt unbuttoned. Everything about it suggests a near future of Dark and Stormies at sundown on a veranda somewhere. This was the beginning of the town’s glory years, when it was the retreat of choice for Grace Kelly and Elizabeth Taylor, who used to arrive by yacht with Richard Burton.  Today, that glamour has faded (it went the way of the harbor’s once-booming banana trade in the 1970s), but it’s left behind a wonderfully romantic afterglow. As you drive down the road of this small market town, you pass elaborate gates in various states of disrepair peeking out from behind tangles of vines, each marking a former great house or abandoned grand hotel.  Now, scattered among them are signs of new developments. These days, the town’s appeal lies in its seclusion from the dangers (both aesthetic and criminal) often associated with the island’s tourist-heavy cruise-port towns, most notably Montego Bay, 120 miles to the west. (Kingston Airport is 67 miles to the south.) It also has none of the stuffiness, the croquet lawns and gin-and-tonics, of Jamaica’s Old World winter break institutions. You won’t find restaurants with white tablecloths and mercilessly inflated Caribbean prices driven up by imported foods. This is the Jamaica where, on a Thursday night, you can drive into town — past the old columned estates — and lose yourself in the euphoric rhythms of a local street party.  Not that the town is short on luxury — and there’s more on the way. Andrew Chapman, a co-founder of Marcus Samuelsson’s Red Rooster in Harlem, recently acquired the nine-acre Ti Amo estate, the former home of Princess Nina Aga Khan, and is reinventing it as a spa. And just down the coast, Tom and Ronnie Elmshirst, a British couple with music-world ties, are renovating East Wind Cove, a property overlooking the eccentric local landmark Trident Castle, into a B&B with a bar and grill area. What they hope to create is a tropical version of Montauk circa 25 years ago: a beach town with good food and no traffic where everyone knows your name.  The bumpy drive through untamed tropical foliage up to the four-room Kanopi House is perilously steep, which only adds to the sense of adventure you get from staying in one of its four so-called treehouses. They’re actually villas perched on stilts high above the jungle floor and furnished with four-poster beds made from tropical hardwood and wicker sofas with fat white cushions. Fully retractable slatted wooden shutters mean you can leave your room open to the sweet-smelling jungle air and fall asleep facing 100-foot banyan trees thickly swaddled in vines while moonlight glances off the waters of Boston Beach, 400 feet below you. kanopihouse.com.  Set high on a jungle-covered hill overlooking the sea, the hotel doubles as something of a musicians’ retreat; there’s a private recording studio on its lower level where everyone from Grace Jones to homegrown mento band the Jolly Boys to Björk (who recorded part of one of her albums, ‘‘Volta,’’ here) has laid down tracks. It’s also why you should make a visit to its Bush Bar, which often hosts visiting artists at cocktail hour (most recently, Florence and the Machine). geejamhotel.com.  An imposing and gloriously kitschy monument to over-the-top colonial style, the Palace is not so much a place to stay as a novelty to be explored. Indeed, with its Jamaica-shaped swimming pool, columned porticoes and lobby decorated with dozens of wire cages (each housing a chattering, candy-colored bird), it looks like a Wes Anderson fantasy of the Caribbean. Its upper terrace, which is painted like a giant checkerboard, is a picturesque setting for an aperitif. (The bar here serves an excellent rum and ginger cocktail.) jamaica-palacehotel.com.  Port Antonio is at its prettiest viewed from the water, especially from a boat afloat this famously and improbably turquoise 200-foot-deep cove a few miles outside town. Local fishermen will take you out for the day on brightly painted wooden skiffs for a lazy ride around the tree-lined lagoon; you can swing from low-hanging branches into the water and explore a nearby bubbling natural cold spring.  Wrapped around an ancient ficus tree, this tin-roof bar inside the sleepy Goblin Hill hotel (a relic from the Port Antonio of yesteryear) is a magical evening enclave lit almost exclusively by strings of fairy lights. There isn’t a scene (though there is a lulling soundtrack of reggae and mento music, and you’ll usually be joined by a few hotel guests huddling over the small candlelit tables), but there are few places more romantic for a nightcap. goblinhill.com.  Eating at Woody’s, a beloved roadside spot, is a life-affirming experience, thanks both to the cheerful hand-painted slogans that cover the wooden walls (‘‘Just be nice!’’) and the simple, reliably satisfying food. The husband-and-wife owners serve excellent hamburgers and vegetarian patties — bright green with callaloo and served with a side of crispy homemade fries — along with cold Red Stripes and good-natured life advice. 876-993-7888.  A short walk from the sandy white horseshoe of Boston Beach, the beloved Jerk Center is a cluster of seven corrugated-roof food stands. Each sells its own homegrown organic meat (usually pork or chicken) slathered in a distinctive spicy sauce, cooked to succulence over an open fire pit and served with fried crushed green plantains. Pair it with fresh coconut water. bostonjerkcenter.com.  The kitchen at this 20-seat bamboo bolt-hole makes some of the best curries on the island, in particular the rich, coconuty shrimp curry, which comes with a choice of rice or roti and is delivered scaldingly hot to your mosaic-top table as you sit surrounded by an eclectic display of military flags and Army paraphernalia. (Its owner is a retired American military man.) Eat in the lush garden, which feels both as wild — and as intimate — as a good friend’s unkempt backyard. 876-451-2095.  It’s not much to look at, but when you want an alternative to the traditional Jamaican menu of curries and strongly seasoned meats, head to San San Tropez. The unassuming patio restaurant, which is owned by an Italian-Jamaican couple, serves bowls of fresh linguine tossed with sweet local tomatoes and homemade thin-crust pizza. sansantropez.com.  A version of this article appears in print on September 27, 2015, on page M2196 of T Magazine with the headline: Jamaica Unplugged. Today's Paper|Subscribe
These days, the way to encounter the Caribbean mainstay has nothing to do with big resorts — and everything to do with having as local an experience as possible.