Curator’s statement
Anguilla will always have a special place in my heart, as it's where I had the honor of standing beside my college best friend on her wedding day, right on the beach at Meads Bay in front of Straw Hat. From that moment on, I fell in love with the island’s easygoing rhythm. It's the kind that invites you to slow down and settle in. The beaches feel untouched, stretching effortlessly along the coast, and the beach bars, warm people, and iconic views make it all feel both simple and unforgettable. It’s that rare balance of upscale luxury that still feels accessible. It's refined, but never pretentious. I still think about sunsets from the lounge at the Four Seasons—those golden, quiet moments that seem to linger a little longer there. In Anguilla, rum punch is the house wine, time feels irrelevant, and the only thing you’re meant to feel is a sense of complete ease.
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Where to stay in Anguilla
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Things to do in Anguilla
Rent a Moke
The best way to experience Anguilla is by exploring it at your own pace. A Moke makes it easy (and fun) to beach hop and discover the island’s hidden corners.
Gwen’s Reggae Grill
Spend a Sunday afternoon here for live music, great energy, and a classic beach bar atmosphere. It’s one of the island’s most beloved traditions.
Four Seasons Sunset Lounge
End the day with a cocktail and take in one of the most beautiful sunset views on the island. It’s effortlessly elevated without feeling formal.
Meads Bay, Shoal Bay East & Rendezvous Bay
Take long, unhurried walks along some of Anguilla’s most stunning beaches, each offering its own unique stretch of soft sand and calm water.
SeaLife Adventures
Set out on a catamaran for a day on the water, cruising along the coastline with stops for swimming, snorkeling, and soaking it all in.
Prickly Pear Cays
Spend the day on crystal-clear water with powdery white sand and a true escape-from-it-all feeling. It’s one of the most memorable experiences in Anguilla.
Places to eat & drink in Anguilla
Enjoying a famous Ocean Echo Rumzie to start the afternoon!
Straw Hat Restaurant
One of those places you go for a long, easy lunch that turns into sunset drinks. Beautiful setting, great food, and the service really makes you feel taken care of.
Sandbar
Right on the beach with a fun, social vibe. Great for sharing tapas, good music, and cocktails that keep you lingering.
Sharky's Restaurant
A bit off the beach path but totally worth it. It feels personal, colorful, and like you’re getting a real taste of the island.
Ocean Echo
Super relaxed and right on the water, perfect for unwinding at sunset. Definitely grab a Rumzie or two—they’re world famous for a reason.
Elvis's Beach Bar
Pure fun! Strong drinks, great energy, and the kind of place where things can get a little wild in the best way.
Sunshine Grill
Easy, casual, and always hits the spot. Great for a laid-back meal when you just want something good without overthinking it.
Need to know
You can fly into Anguilla if you stop in Miami, Baltimore, or Boston first. Otherwise, you fly into Saint Martin (SXM) and you can take a short plane ride to Anguilla, or take a ferry. I like the ferry! It's easy and short (20 minutes).
The Anguilla Card is $55 and allows you to save 10% on car rentals, the ferry, and some restaurants.
Rent a Moke, for the whole trip or even just for a day! You will see them all over the island and it's the best way to see the different parts of the island—and there are so many beautiful parts.
The people of Anguilla are the kindest, and they really are the best part of the island (even better than the sunsets).
Sundays are BIG for live music. Include a Sunday in your stay!
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Jenna Casper
Jenna Casper
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For more inspiration and insider recommendations, visit our Anguilla page.