The first time I saw her, Anguilla didn’t look like much. I was crewing on a sailboat in the Anguilla Passage and was initially unimpressed, until I took a break from grinding winches and gazed islandward. I saw a gently sloping swathe of green, kind of like a badly balanced kitchen table, but no dramatic peaks, no tropical rainforest.

So it got me to wondering.

Along with Mustique and St. Barth’s Anguilla gets more celebrity traffic than any place else in the Caribbean.

Justin Timberlake mentioned it in a song.

My first night on island, doing dinner at Sandy Ground, our waitress took our order and grinned like we were her co-conspirators. “Next table over,” she says in the tone of an insider, “last night. Uma Thurman was here.”

Who else?

Consider this — just for starters: Justin Bieber, Paul McCartney, Sandra Bullock, Ethan Hawk, Michael Jordan, Brad Pitt, Paris Hilton.
So what made Anguilla such an A-list island?

After a few days, I started to get it. Even more to the point, I discovered that Anguilla wasn’t so much an island for A-listers. It was an A-lister in its own right — thanks to a combination of history, culture, geography, accommodations, and cuisine.

After two trips to Anguilla, I made the discovery that it’s easier to find a bad beach on this island (downright impossible) than it is to find a bad meal (absolutely impossible).

One time we did lunch on a hill with great a view of the seas but nothing special about the location. Couple of shops maybe, an old church where kids in a choir practiced.

Check Out Anguilla’s Other Islands

Furnishings were hardwood tables and chairs — something you might see in the kitchen of a local. The paint job – turquoise and lavender – was somewhere between garish and quaintly charming.

But the food … the food…

And here’s the rub: Tasty’s is not on the tourist track, nowhere near the water or adjacent to any of those big resorts.

But chef Carty has been written up in Travel & Leisure, Conde Nast, and Bon Appetit.

One little restaurant.

Then there are the big players. In early 2019, CNN Travel included Pimm’s at Cap Juluca, where you dine right beside the water in an elegant dining room, in a roundup of the most romantic restaurants in the world.

But cuisine’s hardly the only selling point: think hotels, beaches, great bars, almost anything.

Why This Anguilla Beach Bar Is the ‘World’s Best’

Here are a few superlatives, just for example.

Two years in a row Travel & Leisure readers have rated Anguilla the “best Caribbean Island.” Of the publication’s top 25 hotels in the Caribbean, Anguilla boasts four – Frangipani Beach Resort was rated No. 1. Shoal Bay is consistently counted among both the Caribbean’s best beaches and some of the best in the world. CNN Travel has rated a local watering hole called Dune Preserve the “Best Beach Bar in the World” (though that’s a different story).

Part of the appeal of Anguilla lies in her geography, part of it in her geography and history combined.

Because she’s a small island none of the big airlines can land. Most visitors have to first travel to nearby Sint Maarten and get over by ferry or small puddle-jumper planes. That means mass tourism has never been a part of Anguilla.

Geography translates to some gorgeous beaches: 33 of them. Because those beaches are fronted by shallow waters with sand bottom you get waters with colors so beautiful they could make a politician cry — neon turquoise and lime, incandescent aquamarine.

Geography and history have joined together to add another feature to Anguilla’s appeal: the people.

Walk a beach. No one bothers you. Stroll the road. You’ll be safe. Drive the shoreline. A local will wave.

Because Anguilla wasn’t prime plantation land, after Emancipation most colonists left. Locals were able to live with pride, dignity, and self-sufficiency.

But it’s hard to pin down any single reason why this island is so desirable.

So don’t try to figure it out. Instead, pull up a blanket, have a swim, watch the sunset. But be careful when you roll over on that alabaster sand. That neighbor you’ve just jostled might be an A-list star.

Just like you.