This is how Aaliyah died. That’s all I can think as I strap into this 34-seat puddle jumper that will shepherd me the 230 miles from Puerto Rico to the small Eastern Caribbean island of Anguilla, a romantic hideaway renown for spectacular white-sand beaches and robust coral reef systems. This flight is the final leg of my journey, which began more than eight hours ago in Houston with a red eye from Bush to San Juan.
But that was a real plane. This aircraft is disconcertingly similar to the Cessna 402 that crashed in the Bahamas 18 years ago, killing the 22-year-old R&B star (and eight others) after she filmed a music video for “Rock the Boat” on that nearby island.
“We will do our best to ensure a safe flight,” the pilot says. Real convincing, I think. A baby screams, and I wonder what she knows that I don’t. Miraculously I fall asleep. I wake up—unscathed—an hour later at the tiny Clayton J. Lloyd International Airport, which has one terminal (if you can call it that) and no jetways to speak of. There are just a few flights to Anguilla, and only from other Caribbean islands; most visitors fly into neighboring St. Maarten and take a ferry over, arriving in Anguilla quickly, in about 20 minutes.
Anguilla’s relative isolation is part of its appeal. But its exclusivity is something of a double-edged sword for the tourism industry. More flights to the island would make getting here a whole lot easier, but might they also spoil the reward?
Anguilla’s economy depends on luxury tourism, and nearly every resident seems to have some connection to the hospitality industry. Five-star resorts dot the island, which spans just 16 miles from end to end and, at its widest point, about three miles across. Its snakelike shape inspired its name, which is Italian for “eel.” At its navel is the capital city, The Valley, home to the airport, the government, and relics of Anguilla’s colonial past, like the only surviving plantation house, which dates back to 1787.
The 33 beaches that encircle the island’s perimeter—all public—are widely regarded as the best in the Caribbean, and for good reason. A first glimpse at the impossibly turquoise waters here is nearly heart-stopping. They look Photoshopped.
As we leave the airport in an SUV, I take in my first island sights: palms dripping with fresh fruit, pastel-hued houses, and ... oncoming traffic?! The ride is briefly harrowing until I remember Anguilla is a British territory.
“As you can see here,” my driver quips, “right is wrong.”
He proceeds to prime me on the island, home to almost 15,000 people—“I don’t know who they are, but I know of them,” he jokes—and flat: The highest point here is 213 feet above sea level. The mountains that rise in the distance are part of the two-territory island of St. Martin (the French side) and St. Maarten (the Dutch one). The northern coast of Anguilla borders the Caribbean Sea; the southern coast, the Atlantic.
I’m staying along Meads Bay on the West End at a newly revitalized oceanfront retreat in the luxury Auberge Resorts Collection portfolio called Malliouhana, which is the original name of the island, bestowed upon it by Anguilla’s indigenous Arawak population.
Malliouhana was the first luxury resort in Anguilla when it opened in 1984, just four years after British businessman Leon Royden fell in love with the island on a day trip while vacationing in St. Maarten. Then and there Royden pledged to relocate, open a hotel, and retire in Anguilla. He did just that with his Malliouhana, which he continued to be involved with managing until his death at home on Meads Bay, at age 90, in 2014.
A prolific art and wine collector and reportedly a personal friend to Aristotle Onassis—who, with Jackie O, regularly vacationed on the islands, as evidenced by a framed portrait of him in Malliouhana’s lobby—Royden returned a certain level of glamour to this corner of the Caribbean, long touted as a hideaway of the rich and famous. Even today Anguilla retains that quiet romance and serenity. This is not a place for bachelorette parties or blow-out spring breaks—not at all. Even though it possesses all the natural trappings for beachfront debauchery, Anguilla remains, somehow, a refuge.
AS WE ROUND THE BEND TOWARD THE RESPLENDENT MALLIOUHANA, I am so thankful for that. Lined by mighty palms, the path leads to a massive “main house” with an alabaster facade, tall arched windows, and blue-and-white striped awnings. Set against rocky bluffs that dip down to the aquamarine ocean—which spans everywhere, as far as the eye can see—the scene recalls coastal Greece.
Soon I have a “welcome” rum punch in my system, and it’s off to the races. My room—less of a room and more of a “small house”—is among the terrace suites that face Turtle Cove, the most secluded of Malliouhana’s three on-site beaches. I amble along a meandering stone walkway from the main house to my suite, awed by the verdant landscaping and fragrant frangipani the whole way. There are 25 acres for just 63 rooms. The place is brimming with life; tiny lizards scurry underfoot, and there are so many white butterflies it feels almost suspicious. Is this place even real?
My massive oceanfront suite is bright and cheerful, everything from the walls to the floors to the furniture in shades of pale yellow, blue, and white. Unlike with other luxury resorts, there’s little to no branding here—everything feels organic and unique, and of true Caribbean-eclectic design. My place boasts soaring ceilings and giant, colorful artworks, plus an entire wall of double doors that open up to a spacious private terrace with a breathtaking view of the sea in gradient blue hues, all framed by a charming archway. The water looks close enough to lap at my bare feet on the sun-drenched terra cotta; it begins vividly turquoise at shore and becomes a rich, deep cobalt as it extends into the abyss.
Despite being exhausted by travel, I’m overcome by a near primal urge to get in it. Without bothering to unpack, I rifle through my suitcase to find my swimsuit and get out the door as fast as I can. I bound down the stairs to Turtle Cove, which is blissfully empty but for a sprinkling of white wooden beach chairs and yellow-striped umbrellas plunged in the sand. The water shimmers and sparkles as the late afternoon sun begins its descent on the island, and again I have to wonder if this is real.
This is not the unforgiving Atlantic Ocean of my blustery New England childhood. This is a sea that takes you in its arms and rocks you, gently, and before you know it you’re on your back gazing up into the endless blue. There’s something about the salinity of the water that’s pure magic—you’re swimming, then you’re floating, just like that. The sand is powder-soft, and the water is crystal-clear. I could stay here all night and watch the waves kiss the shore, and I probably would if I didn’t have dinner plans.
FOR ME EVERY MORNING IN ANGUILLA begins with a “Meads Bay Breakfast” of fried eggs and sweet plantains, fresh mango salsa, and creamy coconut rice—a singularly perfect meal.
Today, I’m exploring the 35-square-mile island by Mini Moke, an electric version of the iconic, open-air Caribbean vehicle that looks like a baby Jeep. Wind in my hair and sun on my face, I’m whisked from the West End to the East, stopping along the way to take in historic sites and more magnificent beaches. Both are found in Rendezvous Bay, so named for the 1745 incident here in which Anguillans, armed and hiding in nearby bushes, successfully thwarted an attempted French invasion.
This cove is two miles of snow-white sand—and, in one area, what locals call “Anguillan snow”: huge gobs of sea salt. Today a man named Bankie Banx holds court here; proprietor of Dune Preserve Beach Bar and Anguilla’s resident reggae star, Banx is “a cross between Bob Marley and Bob Dylan,” according to my tour guide, Mimi.
Farther east is Sandy Ground, which doubles as the island’s nightlife hub and the site of its all-important boat races. Mimi explains the origins of Anguilla’s national sport—not cricket, and not to be confused with sailing. The racing boats, the most prestigious of which are deemed Class A, are made in local villages and distinctive for their almost comically oversized masts and sails. The popular sport was born here centuries ago, when a massive drought in the late 17th century forced Anguillans to find work on neighboring islands. Many would journey to the sugar-cane fields of Santo Domingo to return in July at the end of harvest. Those left behind would wait for them, and it soon became a competition—with betting involved—to see which boat would arrive first. These days boat races take place in Anguilla during most holiday weekends.
Those early voyages also allegedly spawned Anguilla’s beloved johnny cakes—whose name is technically a malapropism for “journey cakes,” as the cornmeal flatbread was dense and filling enough to become a staple for long sea trips.
Mimi—herself a native Canadian who, like Malliouhana founder Royden before her, fell in love with Anguilla on a visit and made it home—imparts more island wisdom throughout the day, like the local slang “lime,” which means to hang out, and the national truth that “the sea is ingrained in the Anguillan soul.”
IN SEPTEMBER 2017 ANGUILLANS saw the dark side of that truth when Category 5 Hurricane Irma tore through the island, leveling homes, schools, churches, and the only hospital, leaving in its wake widespread destruction to the tune of nearly $200 million.
Despite claiming only one fatality in Anguilla, Irma was one of the strongest storms in history, and it gutted the island—and Malliouhana. Most of the resort, from the main lobby to the landscaping, was destroyed. But rather than simply rebuild, Malliouhana embarked on a multimillion-dollar renaissance. “Probably half of the hotel is now new, and the other half is restored after the hurricane,” says Auberge area director of sales and marketing Alex Batista. The resort went from 44 to 63 rooms, adding two- and three-bedroom suites, a state-of-the-art spa, a beachfront restaurant, and a wedding deck that looks cantilevered over the picture-perfect Caribbean Sea.
Spurred by a shared sense of resiliency and an economic dependence on tourism, Anguillans banded together to rise like a phoenix from the ashes—in record time, all things considered, and by all accounts even better than before. “If you look at other nearby islands, you’ll still see damage from three hurricanes ago,” Batista says. Not so here, where “Anguillan Stronger” became the national motto post-Irma. Residents still bear the indelible scars of the storm, but those are fading every day.
FOUR DAYS OF HEAVENLY OCEAN VIEWS, strong rum, fresh seafood, wave jumping, and sherbet sunsets have changed me, and their imminent end is reason enough to drink. So it is on my last night in paradise that, three new friends in tow, I return to Sandy Ground for one last hoorah.
The destination is Elvis’ Beach Bar, an island institution that began with a beer cooler, a garden hose, an extension cord, and an Anguillan racing boat dragged onto shore and turned into a bar. Thirteen years later it’s added a second bar, a stage, and a full-service Mexican restaurant. It’s also earned spots on the Travel Channel and in the New York Times.
Owner Brett Fetterolf—an American expat who, wait for it, fell in love with Anguilla and decided to make his vacation permanent—named the place for his business partner and head bartender, Elvis, a native Anguillan and known figure around the island, famous for his uniform (basketball jerseys) and his heavy pours.
We dance to Caribbean music, play giant Jenga, and fawn over other customers’ dogs, all while racking up an exorbitant bar bill with repeated requests to Elvis to “make something sweet, frozen, and strong.” He obliges, again and again, even beckoning the four of us behind the bar with him at one point.
Fetterolf lives in a little beach house within crashing distance of his bar, so he can—and does—walk outside to work shirtless and barefoot. This is the island way, and there’s a reason people like him, Mimi, and Leon Royden visit once and never leave. Four days here is more than enough to convince me of their logic: Beyond the unparalleled beauty and easy- breezy way of life, the island also boasts a low crime rate, low taxes, cheap and tasty food, and overwhelmingly warm, congenial people.
I start to think maybe I could actually do this, and how much my life would change if I did. Stress has melted away from me all week, and sure, I’m on vacation, but even if I were checking my email, I just know things would be different here. There’s something in the air, in the water; I barely recognize myself. I want for nothing. For the first time in recent memory, I’m not consumed with a single anxiety, even though my problems still exist. I don’t care! I don’t want to check my phone; I just want to go swimming.
It’s almost as if everyone is vibrating on a different frequency here; they just seem ... happier. Despite the fact that they’re still sorting through Irma’s rubble, virtually every Anguillan I encounter is smiling.
The cruel irony of living in this so precariously positioned paradise is that the captivating turquoise sea, that immeasurably gorgeous abyss that is the heart and soul of this island, is also its worst nightmare. It will inevitably rise up again to knock down what Anguillans have taken such great pains to rebuild, and they know—and maybe accept—this. “Every hurricane makes them stronger,” Batista says. That’s when it clicks: They know what’s important and, most important, what’s really not. They’re forced to be untethered to the material, the earthly, the fleeting—it all quite literally comes and goes in waves. It’s a complete psychic shift.
So, yes, I must move here, for my health. The easiest way to accomplish that, I think, is by marriage. On that Moke tour, it takes me less than an hour to fall in love with Daryl, my unfathomably handsome driver who was born and raised on the island but went to college in New York and, he tells me with a (perhaps imagined) wink, is divorced. Sadly, nothing comes of it—despite my alerting my family, via text, about the prospect of a forthcoming Anguillan wedding. Malliouhana even has that deck! Maybe I jinxed it.
So it’s back to reality—for now at least. On the way back to Houston, I’ll fly out of St. Maarten, so I load up on Dramamine for the rocky boat ride over. Which reminds me of “Rock the Boat,” and the late Aaliyah. Thank God that plane from San Juan got me here safely. I wouldn’t want to die without having seen this place first.
Most visitors fly to St. Maarten’s Princess Juliana International Airport (flights from IAH start at around $500) and take a ferry to Blowing Point, Anguilla’s port of entry, with fares starting at $65 one way, plus a $28 departure tax. United offers one- stop flights (San Juan, Puerto Rico) to Anguilla from IAH starting at around $1,100 (roundtrip).
Malliouhana Resort, rooms from $420
- Malliouhana offers excursions including sailing classes, sea cruises, horseback riding, deep-sea fishing, and cooking with local seafood; book through resort.
- Moke Anguilla (+1- 264-476-5000) offers short- and long-term Moke rentals—just remember, they drive on the other side of the road here.
- Take an unforgettable night tour in a light-up, transparent kayak with Liquid Glow ($75)
- Celeste, Malliouhana’s on-site restaurant with open-air, oceanfront dining. Get blackened mahi, coconut rice and beans, and grilled crayfish—not to be confused with crawfish—a spiny lobster-like crustacean found only in Anguilla.
- Leon’s at Meads Bay, a laid-back island hangout (on Malliouhana property) with live reggae, beach games, and specialty johnny cake burgers. Also try rum-glazed chicken wings and sorrel punch, a rum-based cocktail with house-made sorrel (a tangy herb) liqueur.
- Elvis’ Beach Bar (+1-264-498-0101), the go-to Sandy Ground canteen for Mexican food, famous rum punch, and any frozen concoction Elvis dreams up for you. Just trust him.