It’s barely 6 p.m. on a Friday night, and already there’s a line forming at Oistins. To the uninitiated, the cheerful outdoor fish fry in this sleepy south coast village might resemble an overflowing beer garden. But since the mid-90s, the knockabout local institution first popularized by fishermen and windsurfers has functioned as a tropical Studio 54 of sorts, a riotously diverse melting pot of deep-pocketed voluptuaries and flip-flop wearing locals and action-seekers. The ruddy man in cargo shorts next to you, waiting for his mahi-mahi and macaroni pie, is just as likely to be a German tourist from the all-inclusive down the beach as he is the British billionaire Lord Bamford (he of the 204- foot yacht, Sikorsky helicopter, and $25 million Heron Bay estate), who is evidently not above queuing like everybody else to eat dinner out of a plastic container.

Andre Parris, a chatty twenty-five-year-old radio personality, says he has been coming to Barbados all his life. “My grandmother’s house is literally up the street,” Parris says. He is one of the most in-demand DJs in the Caribbean, used to island-hopping with the likes of British Formula One world champion Lewis Hamilton and Barbados’s most notorious international export after rum, Rihanna. But not on Friday nights. “If you are out early and wondering why everywhere [else] is empty, it’s because they’re all here,” Parris tells me. “It’s a little scrappy, but you always have fun.”

He might as well be referring to Barbados. I started coming to this former British colony in the Lesser Antilles a dozen years (two passports and many rum punches) ago, lured by a vague idea of a gently fading elegance that conjured louche aristocrats and even more disreputable Hollywood celebrities with grand Palladian homes. Of course, by the time I arrived, the island’s heyday had long since passed: when screen legend Claudette Colbert entertained neighbors like Sir Ronald and Marietta Tree (Heron Bay’s original owners) and their friends Bill and Babe Paley at Bellerive, the eighteenth-century plantation house Colbert bought in the early 1960s; and when interior designers Oliver Messel and Happy Ward were the last word in refined tropical glamour.

Even the Concorde—which, along with the emergence of the bikini and the closing off of Cuba, arguably put Barbados on the map—was no longer flying in paparazzi bait like Mick Jagger and Princess Margaret. Although its classic hotels such as the lace-latticed Colony Club had seen better days and an influx of nouveau riche Russians and rowdy booze-cruisers had sent discerning jet-setters scrambling to the chic enclaves of St. Barts and genteel seclusion of Mustique, I kept coming back. Something about this plucky coral island, which emerged from a seismic dustup on the sea-floor nearly one million years ago and went on to survive colonization, slavery, at least one decimating hurricane, and even McDonald’s (which the locals ran out of town in 1966 to protect their bellowed homegrown chain Chefette), remained definitely appealing.

While others chase the next it island, those who stayed—some of whom have been coming back their whole lives—most prize the laid-back civility that still prevails. “It’s so easy and friendly, and now that my kids are grown, everyone always wants to go out and meet people,” says Kit Kemp, the London-based interior designer and co-owner of Firmdale Hotels (including the new Whitby Hotel in N.Y.C and the Ham Yard in London), who has spent several weeks a year on the island since 1986 and owns a house on the historic Sandy Lane estate. Regular as always running into friends at the Sunday market on the polo field at Holders Hill, or over drinks at Scarlet, a trendy west coast bistro bar in a former chattel house on Highway 1. And if you haven’t come with friends, you make them: like the local who, having seen me stranded with a flat tire, didn’t think twice about driving me home in the opposite direction from where he was headed (and who knew my name the next time I saw him). As my friend Emma Snowdon-Jones, a philanthropist who for years divided her life between Manhattan and a Messeldesigned house in St. James, likes to say, “If you want to understand Barbados, sit down with an old-timer outside a rum shop.” At these colorful local watering holes, it’s not uncommon to find visitors talking cricket and politics with the locals while playing dominoes and downing rum and Cokes with ham cutters. (In a divinely Bajan culture contradiction, these shops are usually located a mere stumble from one of the island’s many coral Caribbean Gothic churches.)

That’s the main thing about Barbados: It isn’t some cartoonishly beautiful fly-and flop destination, but a living island whose history is as present and defining as the white clapboard house-lined streets. Ever since the British settled in 1627 and subjugated the inhabitants and the land in the service of sugarcane, the island’s architecture reflected the ambitions of the Crown; it was the headquarters for the fight against French invaders in the late 1700s, and for more than a century served as the Royal African Company’s slave-trading hub for the entire Americas. This explains why Barbados can sometimes resemble a historical theme park, while also giving a visitor a lot to think about, particularly at a time when issues of racial legacy are dominating conversations at home.

“What sets Barbados apart is its remarkable heritage,” my pal Henry Fraser, a senator in the Barbados Parliament and the island’s unofficial oracle, tells me in the “yawny-drawly” delivery that Coleridge once ascribed to the locals. We’re having lunch at the Waterfront Café, a no-frills joint by the marina in Bridgetown, on the island’s southwest coast, one of the best spots for authentic Bajan food like pepper pot (a potpourri of stewed meat), flying fish, and cou-cou (cornmeal and okra). In Bridgetown alone, he says, you’ll find a pair of neo-Gothic parliament buildings, a 363-year-old synagogue (built by Brazilian Jews fleeing the Portuguese), and Wildey House, a Georgian manse that’s now the headquarters of the Barbados National Trust. The group organizes tours of the sagging former homes of castaway lords and ladies and a former prime minister, the rooms stuffed with musty antiques and curios as well as elegant silverware and china straight out of a Christie’s catalog. In recent years, the stories of these houses have been fleshed out to include the narrative of the slave population, on whose backs the island’s economy was built. “For a while, I think we ran the risk of becoming the Caribbean version of Downton Abbey,” quips Miquel Pena, the affable head of the Trust. “You often only heard the story of the white owners. The fully story has to be included in all its complexity.”

This story is something that the island had to reckon with in the lead-up to last November’s fiftieth anniversary of independent statehood, which marked cultural and historic milestones back to Barbados’s 1652 treaty with the British (which supposedly inspired a few lines in America’s own Declaration of Independence) and culminated in a guns-blazing concert by Rihanna. The island’s economy, based predominantly on tourism but buffered by trade as well as foreign investment, is relatively robust in spite of the Caribbean’s recent Zika-related woes.

But to glimpse the future of Barbados, you could do no better than to head to deAction World, a surf shop/café painted in Looney Tunes colors. Owned by Brian Talma, a former professional surfer who windsurfed for Barbados in the 1988 and 1992 Olympics, deAction is located on the south coast—at a safe distance from the island’s hedonic touristic nightmare at St. Lawrence Gap—an area that’s becoming increasingly popular with young locals and travelers who come for the world-class waves. As a result, a few new hotels and boardinghouses have recently opened, bringing considerably more affordable options than on the western Platinum Coast.

“When I opened up here twenty years ago, people thought I was totally mad—it was like the Wild West,” explains Talma, who at fifty-one still resembles a young beach bum, with his slender surfer body and mop of blond corkscrew hair. “But I kept insisting that the beach culture here is special. What we have now is an organic, healthy way of life that involves the local community—it’s thriving.”

As if on cue, a group of hard-core surfers from Ireland carrying boards stop on the beach to ask where the best waves are breaking. While Talma prepares to show an Aussie novice how to paddle out, he responds in his Bajan lilt that “Bathsheba”—an alluringly choppy beach on the rugged Atlantic coast—“is where deaction is.” A young black couple from San Diego ask about the best place to eat nearby. “Chicken Rita’s!” shout a chorus of local surfers sitting in the shade, referring to the legendary rum shop where punters patiently wait for the best fried chicken in town. Meanwhile, a well-turned-out older British couple approach, holding hands—a picture of gentility marred only by the Rottweiler they restrain on a tight leash.

As he begins the surfing lesson, Talma tells his pupil not to overthink it, to leave it all out in the water. “Out here,” he tells him, “we’re all the same.”

Barbados On and Off the Beach

Like every Caribbean island, Barbados empties out during the summer, then crowds return for the season starting in late October or November. Arrange a car through Top Car Rentals or have your hotel hire a driver so you can easily explore the island.


If it’s scene cuisine you’re after, look to the west coast; Beachfront Lone Star is great for Sunday lunch and rubbernecking Brit regulars like Simon Crowell; newish Cin Cin by the Sea has staying power, if the cult-like veneration of their pork buns is any indication and the chic crowd all seem to wind up at Italian hot spot Daphne’s. To my mind, though, no meal compares with those at The Cliff, where chef Paul Ownes has turned out elevate Caribbean since 1988. It’s undeniably pricey, but the view of the lighted cove below is worth it.

For casual options, Kit Kemp likes Good Choice Chinese, in Holetown. If you have a few hours to kill, she adds, go farther south to Lobster Alive, a nondescript shack on the beach, for evening jazz.

If you’re up in the northwest near the parish of St. Lucy, stop in at the Fish Pot, set on the water in a seventeenth-century fort. In season, it’s the place to try the Bajan specialty grilled barracuda with drawn butter.

At night, if you’re in the south and not feeling Oistins again in the town by the same name, or head to Café Luna, on the roof of the Little Arches Hotel, for a solid Baja three-course menu, including flying fish coconut shrimp.


Barbados is where the Caribbean and Atlantic collide, and the west coast gets most of the love, with stunning turquoise beaches behind practically every hotel. Take your pick, but I have a soft spot for Payne’s Bay near Sandy lane; its quiet surf feels made for swimming and snorkeling.

Most locals will tell you to venture farther. Though hardly secrets, Accra Beach, Dover Beach and Brandons offer relative seclusion from the crowds and street vendors. There are several surf schools in the area, but deAction Shop & beach Apartments in Silver Sands is ground zero for the islands beach sports scene.

And you absolutely have to stop at Bathsheba on the east coast, one of the top suffering spots in the world. The water is too dangerous to swim in, but the tide pools are perfect for cooling off. Park as the nineteenth century Round House Inn and Restaurant up the hill, a good spot for and afternoon drink.


If you’re into snooping around historic homes, you’ll love the Barbados National Trust’s open houses each Saturday during the season.

Up north in St. Lucy, the Animal Flower Cave so-called for the oxidized green and brown formations that look like lizards and turtles, is worth exploring. Or if the only holes you’re interested in are on a golf course, Barbados has several world-class ones, including three at Sandy Lane, where you might spot one often famous green monkeys.

This being “Little England,” polo remains hugely popular, attracting top international teams from January through May. There are four polo fields on the island, with the Barbados Polo Club in Holders Hill (the former family home of Johnny and Janet Kidd) and the everexpanding Apes Hill Polo Club in St. James the most popular for lessons and watching world-class events.


Any conversation about hotels in Barbados inevitably comes back to Sandy Lane, the pink-accented, Happy Ward-designed neo-Palladian grandee dame that has defined luxury on the island since 1961. When I first went there in the early aughts, the place had stumbled a bit, but the sprawling 300-acre estate regained its footing after a renovation and remains the place of myth; the airport transfers in the house Bentley; the opulent rooms; the solicitous service at its four restaurants’.

Conjuring the romance of the islands British past the family-owned eighty-eightroom Coral Reef Club sits on twelve manicured acres, the beach club is the most pleasant on the coast-everything you need within reach, without the crowds of the bigger hotels.

A little farther up the forty-room Cobblers Cove is chic and discreet. I highly recommend staying in. Camelot at the Great House, a suite in the former private residence that anchors the property. Another favorite, more geared toward couples and small families, is Little Good Harbor, with its whitewashed stone cottages, top-notch spa, and one of the best restaurants on the island, the Fish Pot. If you’re looking to avoid the hustle of the west coast, the rugged east coast has one iconic mainstay, The Crane, on a world-famous beach. Built in 1887, it’s a little big for some tastes, but it’s hard to fault the rooms of the rambling environsthere’s a reason fashion photographers have used it as a backdrop for decades.

Renting a villa may be the best way to experience life as a local, and there’s never been a better time, as there are a number of empty grand estates that owners are opening up. Sir Paul Altman, of Altman Real Estate has some of the best options, including historic plantation homes and beachfront properties.