Where To Eat, Drink, & Stay

When I arrived in Anguilla, I expected to have a nice, relaxing time sipping on piña coladas and gazing into the crystal-clear aquamarine water. You know, like any standard beach vacation. But those four days I spent on the tiny Eastern Caribbean island proved to be way More chill than I anticipated. I left feeling as if both my mind and body got a complete reset.

It may not be the first island that comes to mind when you think of destinations in the Caribbean, but the British overseas territory offers so much within its 39.38 square miles. If you’re the kind of traveler who likes to explore and be active the entire time, there are plenty of excursions you could take (my favorite was to Prickly Pear, a tiny island that’s a half-hour boat ride away). You don’t even have to venture out very far for good snorkeling; I saw rainbow-colored tropical fish and turtles right off the shoreline of my resort. You can take cooking classes and learn how to make ceviche using local mahi mahi. (I did that and highly recommend it.) There are spas you can visit to get a facial or Swedish massage. Or you could simply laze about on the beach and enjoy the most gorgeous ocean you’ll ever lay eyes upon.

You can’t fly directly to Anguilla from most places (though you can from Miami), which probably explains the fact that the island isn’t as packed with tourists as its neighboring Caribbean spots. To get there, you’ll have to fly to Sint Maarten and then take a public ferry or private boat. Something worth noting: You’ll have to clear customs at both islands, so be sure to fold in plenty of time for that. But all schlep-induced stress will melt away as you get a glimpse of the white sand, glassy ocean, and breathtaking views the country has to offer.

Where To Stay In Anguilla

I was invited by the Four Seasons Anguilla to stay at its resort, a sprawling oceanfront oasis with suites and ocean-view villas (rooms start at $1,895 a night), multiple restaurants, a spa, and three pools — one of which is infinity-style overlooking the ocean. Whichever kind of room you book, you get a private plunge pool in your sundeck, just to give you a sense of the many niceties you’ll experience at the resort. It is a Four Seasons, after all — a hotel brand renowned for its top-tier luxury hotels around the globe. But its Anguilla location is exceptionally special: as soon as you enter the resort, you’re struck with its minimalist, airy, modern design. The open layout of the reception pavilion lets your eyes feast upon a neatly manicured lawn, with giant palm trees and straw lounge chairs spaced out every few feet, that extends all the way to the ocean at the horizon.

When you walk along the lawn, you’ll come across two of the resort’s restaurants. One is Sunset Lounge, which features Asian-inspired dishes, a live DJ at night, and, well, the best sunset views. the other is salt, a contemporary restaurant that sits atop the bluffs the hotel rests upon. When I came there one evening, I looked over the railing next to my table to see a stingray and a sea turtle floating about in the ocean below. You’ve also got two more casual dining options: Bamboo Bar & Grill and the Half Shell Beach Bar, both of which are located on the beach. Pro tip: Order the shrimp tacos at the former and skirt steak skewers at the latter.

What To Do In Anguilla

Without leaving the Four Seasons, I could do practically anything I could dream of. Get my R&R on next to a pool or beach? Check. Indulge in some water sports? Done — I went snorkeling, but the hotel also offers scuba diving, paddle boarding, windsurfing, kayaking, and boogie boards. You could also stay active at the resort’s fitness center or sports pavilion, the latter of which houses basketball, volleyball, and tennis courts.

One of the hotel’s main draws is its 8,800-square-foot spa. The two-story villa has 13 treatment rooms where you can get anything from a coconut-oil-infused scalp massage to a body scrub, facials, and more. While I was there, London-based acupuncturist Sarah Bradden was in residency offering her signature Bradden Method treatment — a wellness potpourri that incorporates both regular and cosmetic acupuncture, reiki, LED light therapy, reflexology, and ear seeds. I had never experienced a more relaxing treatment — of any kind — in my life. Still, even though she’s no longer in Anguilla, other famous wellness gurus and aestheticians regularly cycle in through the spa. Case in point? Four Seasons is currently partnering with New York City wellness hub The Well on a retreat at the resort that features breathwork, meditation, and movement.

Foodies have plenty to do on the property, too. You can book cooking classes, where you can learn how to make things like Johnny cakes, a staple cuisine in Anguilla that’s basically Caribbean-style cornbread. And besides the (amazing) food you can get at the resort’s four restaurants, you could venture out to explore local fare at Blanchard’s, a nearby beach shack with things like jerk chicken, burgers, mahi mahi bites, and rum punch cocktails.

I also recommend taking a day trip to Prickly Pear Island, a tiny spot just 6 miles away from Anguilla that you can access by ferry. I didn’t think I’d see a prettier beach than the ones at the resort, but Prickly Pear’s managed to do the trick. It’s extremely small, but it’s much less crowded. All that’s there are beach chairs, a shack-style bar, and a casual restaurant that serves the best lobster I’ve ever had. And you can experience it all as you gaze into the clear cyan-blue water that goes as far as your eyes can see.

For those craving a nightlife scene or a cool bar where you can sip on the island’s signature rum punch with other travelers, hit up Sandy Ground, an area near Mead’s Bay that’s rife with bars and restaurants. My fave spot was Elvis’ Beach Bar, a lively place Where you can enjoy cocktails, bites, and live music right on the beach. Part of the bar was actually a boat that was remodeled into a really cute place to drink margaritas (and take pics for Instagram).

Tips For Traveling To Anguilla

If you’re willing to deal with the trek, traveling to Anguilla is well worth it. Note that the US dollar is widely accepted, but the local currency is the Eastern Caribbean dollar ($2.7). EC equals $1 USD).

Staying at an inclusive resort like the Four Seasons makes life easy once you get there and offers something for whatever kind of vacation mode you’re looking for. But if you want to explore beyond whichever hotel you stay at, hit up the #Anguilla hashtag on TikTok or Instagram for tips on the must-visit destinations on the island. Wherever you end up, I guarantee that you’ll have an unforgettable time.