Okay, Revolution Gray community, who’s up for traveling to Anguilla with us?

St Barts, Mustique, and Barbados might grab all the attention, but the lesser-known Caribbean islands, like Anguilla, often have more to offer.

Let’s take a look at this little island’s big appeal from rustic street food to the latest luxury residences.

If Barbados and St. Barts are the celebrities of the Caribbean—the brash, flash ones who attract all the attention, then islands like Anguilla are their aristocratic counterparts—understated and discreet, with a panache all of their own.

To date, this tiny country, one of the most northerly of the Leeward Islands, has kept a relatively low profile, but the A-list is starting to discover its appeal. Robin Williams and Robert de Niro were just two big-hitters known to stop by for lunch—Anguilla’s gourmet restaurants being one of its major attractions.

There are other features, too, that distinguish this little island from its better-known neighbors. First of these is that it remains private and unspoiled. Come the winter holidays, you won’t find mobs of people crowding its beaches and bars. It isn’t packed with cruise-boat tourists. Here, you truly can still get away from it all.

And the beaches themselves really are something special. There are 33 of them in all–sugar-white stretches of soft sand that often continue for a mile or more. Shoal Bay, in the northeast of the island, is a two-mile stretch that’s consistently voted one of the best beaches in the Caribbean. Condé Nast Traveler describes it as ‘amazing… It manages to feel alive and animated without being in the least crowded or overbuilt.’

The weather here in Anguilla is idyllic, too. Many Caribbean islands are mountainous, which means they’re often cloudy and rainy. Being flat, Anguilla has a much more agreeable climate. The temperature hovers between 23°C and 31°C year round, while the waters hover in the high twenties, even in January.

And activity-wise, the island delivers plenty to do. The snorkeling and diving are, as you’d expect, first-class. The clear, turquoise waters offer up a huge variety of sea life to explore–you’ve got six marine parks and nine wrecks to dive, including that of a Spanish galleon. One of the best dives is the Osterdeep wreck, which goes down some 80 feet and lets you swim among turtles, eel, (small) sharks, and stingrays.Anguilla-beaches-CaribbeanMeanwhile, boat racing–not cricket–is the national sport, with almost everybody either taking part in or watching May’s and August’s big regattas. And though August is considered off-season, it’s actually one of the best times to visit, coinciding with Anguilla Carnival, the island’s most important holiday–a week of parades, pageants and parties that’s a bigger deal than Christmas.

When it comes to nightlife, Anguilla isn’t a dusk-til-dawn party destination, but it still knows how to have a good time. Sandy Ground, another of the island’s most popular beaches, is home to a clutch of lively bars and restaurants, like the Pumphouse, a classic beach bar that serves up tropical cocktails with a side order of rock’n’roll.

And just a short stroll away is legendary restaurant Johnno’s, which has been an institution here for more than 20 years. Go on Sundays for live jazz and lobster.

You’re also only a 20-minute boat ride from St. Maarten, with its clubs, casinos, and tax-free shopping. Prices are around 15-30 percent cheaper than those in the US, with deals to be had on cameras, watches, and clothes.

This beautiful island offers an escape from the standard fare. Here you have the chance to experience the real Caribbean, only with some of the world’s finest hotels, restaurants, and beaches on your doorstep.

Have you been to Anguilla? Let us know!


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Join our growing community of women who are breaking down aging stereotypes and
creating a fresh perspective toward embracing life after 50.