A quest for the ideal leads to Anguilla, where 33 stretches of sand compete for top honors. 

By Becca Hensley
June 09, 2016
Hard to reach, and worth it: Anguilla's Little Bay
Photo: Jerome Louden/Cavan Images

In a thatched-roof beach bar on Anguilla’s Sandy Island, a perfect round of shell-littered, cloud-white sand, I do some math. You’d think I’d be distracted by the whorls of ink-blue waves before me, their undulations like a beckoning hand. Or by a nearby vacant hammock, strung between two coconut trees and gently swaying in the briny breeze. Or perhaps most pressingly, by a heaping plate of lobster and crayfish that’s just arrived, along with an icy cup of rum punch.

Here’s my challenge: In addition to this circle of paradise I’m currently occupying, 32 more beaches make up Anguilla, known among the sand-struck cognoscenti for having the most beautiful beaches in the world. I’ve set out to find the best of the best. Can I possibly see them all in one visit, much less find the nonpareil? I’m here to try. But the algebra taunts me. If I’m to continue my quest, I’ve got to get going.

I pry another forkful of sweet, freshly grilled lobster out of the shell, regard a Renoir palette of startling sea blues, and feel the stealthy gravity of a matchless beach work on me.

Okay, a few more minutes.

Composed of 16 miles of coral and limestone, Anguilla sits six miles north of St. Maarten in the Lower Antilles, at the northernmost point of the Caribbean. Unpretentiously sophisticated with a peaceable zeitgeist, Anguilla didn’t have electricity or telephones until the 1960s. When the sleepy oasis attracted the attention of the yachting set a few decades ago, it didn’t let fame go to its head. With vision, the government banned large cruise ships, casinos, duty free shops and malls—a move that has kept the terrain down-to-earth and pristine.

Related: As the Caribbean Rebuilds, Now Is an Important Time to Visit

That island-wide adherence to restraint has protected Anguilla’s native gifts: sand as fine as fairy dust, with sea grapes and palms proffering shade among quiet resorts, villas, and homes. Often, the beaches link, so walkers can perambulate from one to the other—and back again. Most can be accessed through the back door of hostelries, or entered by means of public footpaths. Some, like the one I’m dallying on, encircle little offshore cays.

My quest calls. I join a boat heading back to the main island, to Sandy Ground—perhaps Anguilla’s most social beach. Mottled with small wooden piers and beach bars, it’s the veritable living room of the isle, particularly after the sun goes down and visitors and locals come to drift among venues, buying conch soup from makeshift stands. In the relative quiet of daytime, it’s easy to spot my driver, Accelyn Connor, chatting near the dock. Accelyn is so well known on Anguilla that wherever I am, all I need to say to anyone is, “Can you call Accelyn?” His small circle of men gently opens to allow me to join. “What’s your favorite beach?” I ask, suddenly. They pause, considering my question. “That depends,” they say, seriously.

Accelyn himself has been to all 33, he tells me later as we bump down the road in his van, dodging chickens and goats. “Can we do it? Visit them all?” I ask as wide-eyed and ebullient as a child. He just laughs, and takes me to another expert, and another stellar bar… and beach.

On the tawny crescent of Crocus Bay, we meet musician (and former professional cricketer) Omari Banks for a drink at da’Vida Bayside Grill. “What’s your favorite?” I ask him, while watching the shadows of some passing clouds scud across the sand. “Well, this one’s nice, but I like Little Bay,” he says. “Because it takes some effort to arrive.” That’s an understatement. Just up the coast from our spot on the midsection of the island, Little Bay is tiny as well as isolated by a tight embrace of towering cliffs. There used to be a rope to anchor the steep descent, but approaching by boat seems the best move. I make plans with a yacht-blessed friend on the island to salute Little Bay tomorrow at sunset, with champagne. This research is proceeding nicely.

The bleach-white shoreline of Maundays Bay
Photo: Annie Schlechter
Great House Beach Resort in Rendezvous Bay
Photo: John Cullen

Sunrise yoga the next morning, at the bleach-white Moorish resort of Cap Juluca on tranquil Maunday’s Bay, adds to my roster. I leave my third eye to handle the meditations, peering down the beach to watch other guests gallop on horses through the gentle waves, the talcum curl of land their path. Fairly perfect, this vista. Check.

But Accelyn and I are far from done. We explore the spoils of some of the island’s other resorts. On Rendezvous Bay, we stroll two miles of cream-colored sand edged by the aquamarine Caribbean that’s home to CuisinArt Golf Resort & Spa and reggae superstar Bankie Banx’s shipwreck-chic Dune Preserve Beach Bar. Velvety and expansive Mead’s Bay, bookended by the just-restored, classic Malliouhana Resort and the Miami-esque Viceroy buzzes with happy paddle boarders and equally happy lounge-occupiers.

The next morning I give Accelyn a break and get a catamaran lift to snorkel a coral reef off the Prickly Pear Cays, a pair of evocatively uninhabited little “wildlands,” as they’re called in environmental circles, which are six miles offshore. And from across the shimmering turquoise, they look just that: scrubby and beautifully wild, with smooth sweeps of white forming ribbon boundaries along their edges.

The variations on what we’ve all pictured as the perfect castaway beach continue to multiply. That afternoon, Accelyn and I join forces again to wander the palm-studded, feather-white sand of Shoal Bay East at the island’s eastern end. At nearby Island Harbour, a fishing hamlet rife with colorful wooden boats, we stand on the pier and wave flamboyantly across the water to owners of a restaurant on Scilly Cay, a teeny dot of a coral island on the harbor’s outer reach. This is literally how it works: they spot our crazy gestures and zip their bright blue open boat over the water to pick us up for a visit and a drink at their bar.

Rum at hand, I return to my math. What I really need, I realize, is 33 days, not a handful. I want 33 languorous visits, one day for each beach. In fact, I want more than that; I want to know Anguilla’s beaches like Monet painted the Rouen Cathedral—in every type of weather, in every type of light. Is this a month sabbatical (give or take)? Is it a life-changing move? Suddenly, I see what my Anguillan friends mean when they say, “It depends.” It’s sneaky shorthand for what a beach really is: a canvas for experience, a portal to possibility. On beaches, I feel both large and small, both lonely and fully connected, both relaxed and recharged. That’s the magic of a matchless beach. Especially, I’ve learned, in Anguilla.

Fresh lobster and beer, Shoal Bay
Photo: Melanie Acevedo/Getty Images 


Easily accessible by air and by sea, Anguilla's main gateways are Puerto Rico and St. Martin, from which private planes, charter ferries, or scheduled public ferries whisk you to the island.


Check in to one of the island's original luxury resorts: Cap Juluca, with its beachfront Moroccan villas and stellar service (rates start at $595; 888-858-5822 or capjuluca.com) or the elegant, recently renovated Malliouhana, An Auberge Resort (rates start at $525; 877-733-3611 or malliouhana.aubergeresorts.com).


Veya in Sandy Ground features specialties from equatorial countries. Jacala (264-498-5888) updates classic French and overlooks Meads Bay. The Restaurant at Malliouhana marries Caribbean spices with sea-to-table catch.


Anguilla's many (and excellent) beach bars are as cool as its beaches. Favorites include The Restaurant on Sandy Island, da'Vida Bayside Grill on Crocus Bay, Scilly Cay, Trattoria Tramonto on Shoal Bay West, Elodias on Shoal Bay East, and Johnno's Beach Stop and Elvis' Beach Bar, both in Sandy Ground.