Anguilla, For the First Time Again

This is the preview of our Anguilla destination guide on Way to Go, our reader-supported email newsletter. To get the best of of our travel recommendations, please subscribe.

Anguilla was the first Caribbean island I experienced as a traveler. I was 24, alone, and totally broke. I had just gotten a big job after a bout of unemployment, which was how I justified treating myself to a trip I couldn’t afford. Arriving at night in the height of a steamy July, I told the taxi “Meads Bay” and let myself into the condo my father’s friend had loaned me. I went to bed not really knowing where I was, and hoped for the best. 

When I woke up the next morning, I discovered that I had landed in a paradise of expansive white sand and calm blue seas, and for a week I did little more than swim, read, nap, repeat. My sole splurge was a lunch at Malliouhana, the fancy hotel at the end of the bay, where I ate a bouillabaisse that would linger in my mind for decades to come.

Last winter I returned to Anguilla as a guest of Anguilla Tourism for the first time since. (Speaking of decades.) I thought it an uncanny coincidence that I was heading back to Meads Bay in West End, until I learned that the bay is the main tourist strip — bookended on the west by Four Seasons Resort and Residences Anguilla and on the east by Malliouhana (still going strong!), with the condo where I had stayed (today the three-star Carimar Beach Club) in the middle  — and that West End is Anguilla’s most densely populated area. 

Of course, “densely populated” is relative when you realize that no more than 15,000 people live on the 35-square-mile island. And while Meads Bay is considerably more developed today, I was happy to see that, on the whole, Anguilla has steered clear of anything resembling the overtourism and overdevelopment that has plagued too many of the world’s beautiful places. Here’s hoping things stay this way, because this island is a cool and mellow jewel. I can think of few better destinations when the vacation agenda is swim, read, nap. 

Although now I’d add a few more activities: tour, sail, eat.

The rest of this article is for subscribers. Sign up for our newsletter, Way to Go, for your all-access pass.