In this Eastern Caribbean delight, you’ll find blissful bays, white sand, cool rhythms and warm welcomes. Just head to St. Martin and turn left.
Settling into Anguilla, our little private pool overlooking Crocus Bay was just the right refreshing temperature and ditto the meltiness of the gin and tonics. And there would be time for another while we waited for the private chef we had hired for the night to work his magic in our glassed-in kitchen.
This British island just north of St. Martin/St. Maarten has one of the highest rates of repeat visitors in the Caribbean. And for good reason: The beaches are insane, the food is phenomenal, and the people are charming—a sun-spot’s triple threat. Anguilla has the right amount of semi-poshness to make it luxe, mixed with just enough normal to make it affordable.
Set up at CéBlue Villas. This gorgeous hillside resort sports five-bedroom homes, each with its own little pool, media room, kitted-out kitchen and gorgeous ocean view. It’s far enough away from it all to enjoy the serenity, but just a few minute’s drive from the heart of the island action. The Crocus Bay beach is just down the hill, complete with attendants, ample watercraft for those inclined, and Da’Vida, a cool beachfront restaurant.
Pop into the posh. The Kelly Wearstler-designed Four Seasons Anguilla is beyond dazzling. Sunset at the Sunset Lounge couldn’t be more special. People flock to this elegant waterfront bar overlooking the infinity pool at cocktail time to see how the other half lives and to prime the night with the signature Jalapeño Margarita.
Set sail. I highly recommend an afternoon of sailing from bay to bay aboard the classic sailboat Tradition, a handmade wooden boat from 1978. Book a trip to Prickly Pear Cay or Little Bay and enjoy a lobster lunch or hop on for the sunset cruise. Mind the fizzy doesn’t go to your head.
Get Scilly. Earmark Wednesday or Sunday for lunch on Scilly Cay, a tiny coral islet off the village of Island Harbour, reachable by a free, 10-minute boat ride. The whole island is a rustic open-air restaurant run by the Wallace family, who whip up Anguilla’s deadliest rum punch, plus platters of barbecued lobster, snapper and chicken. Have a punch, have lunch, then wallow in the shallow waters on the soft sandbars.
Go dancing. Live music is a huge part of Anguillan culture. Locals and tourists lap up reggae, jazz and R&B bands almost every night at the many venues scattered around the island, including the Powerhouse, Johnno’s Beach Stop, Gwen’s Reggae Grill, and the Dune Preserve, owned by music icon Bankie Banx. Time your visit to coincide with the annual Moonsplash Music Festival in March/April.
When You Go. Off-season between May and August is the best time to visit Anguilla to get prime deals and avoid the rains. Book a sea shuttle in advance to get you from the airport to Anguilla via the 25-minute ferry, which runs all day. Keep an eye out for Denzel Washington and Robert DeNiro. No, not together. Go to ivisitanguilla.com for more.