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Three Days in Anguilla

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For years, the Caribbean jet set has been swearing that Anguilla is the next St. Bart’s. Which is rather moot because those who know the islands know that to do St. Bart’s, you should start or end in Anguilla.

This bit of the British West Indies sits north of St. Bart’s and is separated only by the mass-market St. Martin. Anguilla is roughly the size of Manhattan, 16 miles long and 3 miles wide, and is shaped like a bloated alligator. Yet the island has innumerable draws. It’s stroked by 33—yes, 33—pristine white-sand beaches. There are enough varied food joints to keep a Michelin critic happy for ten days at least. If there is one West Indies island where the love for the sea and sailing is more revered than cricket, Anguilla is it. The island adores a regatta. And nothing beats catching some rays on Rendezvous Beach and looking out agog at some superyacht on the azure horizon.

So whether you G5 it into the Clayton Lloyd International Airport or choose to loll on a boat at sea, here is a quick dossier on how to amplify the Anguilla long weekend.

Day 1

There is no better way to start the first day of an Anguilla roam than with a sunrise breakfast at the Straw Hat ( for coconut-water smoothies and a platter—a kaleidoscope—of the freshest fruit. Over on Maundays Bay, Blue (264/497-6666), at Cap Juluca resort, is popular for its Euro-style spread. The fluffy French toast swathed with local bananas will start any morning on a sublime note.

One of the 33 beaches that dimple Anguilla is there waiting. Indulge, albeit briefly. Then ask your concierge for a driver and his Cadillac Escalade to lead a tour of Anguilla’s Heritage Trail, if only to see for yourself Big Spring in Island Harbour, which is at least a thousand years old. If the petroglyphs and rock carvings do not impress, a pit stop at the Heritage Collection Museum (264/497-4092) will. Don’t miss the Lynne Bernbaum Art Gallery (

After the civics lesson, fully embrace your reason to be in Anguilla. Yes, the sea, the sun, the food. Lunch is meant for liming—which is to say making it long and leisurely. Head to the brasserie Le Bar (264/772-3229).

It’s been a long day, so tuck in at brand-spanking-new The Reef by CuisinArt (rooms from $500;, the latest luxe addition to the famed CuisinArt Golf Resort & Spa (rooms from $550; Another new property is Shoal Bay’s Manoah Boutique Hotel (rooms from $370;, which locals have dubbed the Pink Lady after its facade. For the luminary who never travels without an entourage, the Presidential Penthouse is yours for the asking.

Day 2

If your night was spent at The Reef, then order in a quick coffee and get the concierge to have a shuttle cart waiting to take you across the landscaped CuisinArt property. You can have breakfast waiting for you on the crescent beach, cooked up by the resort’s executive chef, Jasper Schneider, who will cater to your every whim. Morning options: a quickie Hydroponic Cucumber & Aloe Wrap facial (only 50 minutes) at the Venus Spa or a round of golf at the Greg Norman–designed 18-hole course.

In the afternoon, hop in your tender and go west around Sherricks Bay to Sandy Island, where a plethora of megayachts by Sandy Ground harbor are all ready for their close-up. And what better setting to view them than over a lobster lunch on a tiny spit of sand that even Robinson Crusoe would envy? At Johnno’s on the cay (264/497-2728), soak up the Caribbean sun, splash in its waters, and dig into fresh lobster and rum punch served up by Anguilla’s beach-party pioneer.

Then head back to Rendezvous Bay for chef Joe Richardson’s sushi at Tokyo Bay ( Don’t resist the tuna and foie gras nigiri or the yellowtail with caviar if they’re on the menu! Close out the night over champagne cocktails along the open-air foyer of CuisinArt.

If you happen to note a cool dude holding court, looking like a cross between Keith Richards and Bob Marley, it’s probably the most famous Anguillan on the planet— Bankie Banx. Schmooze the local reggae-rock star. He lives in grand island-vibe style next door at his fabulous Dune Preserve ( beach bar compound. It’s well worth your own special tour from the maestro himself.

Day 3

How about a roadside breakfast and a chance to mingle with some of the most hospitable folks on the planet? Shoal Bay’s Hank’s Beach Restaurant & Bar (264/497-3137) is a must. The mimosas start flowing at 8 a.m. Pair one with local street food such as the Loco Moco (hamburger patty served over rice and topped with eggs and gravy). Or you could begin the day at the Four Seasons Resorts and Residences Anguilla (rooms from $550; Dining at the Bamboo Bar & Grill is a great choice.

Time to be mesmerized by, in my opinion, the world’s No. 1 leading new spa, the Zemi Thai House ( at Shoal Bay. All treatments adhere to the ancient healing traditions of the Taino people who first lived on Anguilla. The retreat is nestled inside a centuries-old Thai house that was shipped from Thailand to Anguilla over the course of almost a year.

All night, everyone’s at the beach-barbecue at Malliouhana (rooms from $425; malliouhana.auberge, where executive chef Marc Alvarez has set the new standard for gastro-tourism. The party is outside, under the stars, where the crayfish, lobster, conch, and kebabs are prepared over an open-fire grill fueled by local breadfruit wood. Sate yourself with one of the most extensive wine collections on the island. If intimate is more your style, try Veya ( It’s like dining in a tree house! Chef Carrie Bogar and husband Jerry are Pennsylvania expatriates and the epitome of those who visit Anguilla and end up not leaving.


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