How to describe Anguilla? The picturesque 16-mile-long Caribbean island truly makes vacation dreams come true, especially for foodies, design aficionados and beach aficionados. People come to this quiet, uncrowded island for its rich food scene, beautiful boutique hotels and 33 ( !) picturesque white-sand beaches. Did we mention flights starting at $135? If you’re ready to book tickets, here’s our guide to where you can stay, eat, drink, etc
AXA Hike Life
Want to see a side of Anguilla that you might never have discovered on your own? Book an adventure with AXA Hike Life (just DM them on Instagram). Their intrepid guides will lead you through the rainforests, caves, cliffs and scenic trails, and incredible secret beaches of Anguilla. Start analyzing annotations now.
Calypso Charters Anguilla
Whether you’re looking to reel in some mahi-mahi, snorkel in a secluded turquoise cove, explore one of Anguilla’s uninhabited islands, or sadly need a shuttle back to St. Maarten to catch a flight — Calypso Charters electric fleet and skilled captains are ready.
It’s hard to choose from the 33 options, all of which are open to the public and most feature great beach shacks. Our favorite places for lunch/double beach are Blanchards on Meads Bay, Nat’s Place on windy and remote Savannah Bay, and live music at Madeariman on Shoal Bay East.
Owners Jerry and Carrie Bogar are living everyone’s Caribbean dream after leaving their Pennsylvania-based diner to open one of the island’s best globally inspired restaurants. Chef Carrie’s can’t go wrong with fried snapper, lamb and lobster. Late at night, head downstairs to the Moroccan cocktail lounge for live music and killer cocktails.
This comfortable, secluded beach shack in Island Harbor is well worth the walk. Owner and fisherman Warren “Mutt” Webster plunges into his daily catch while the chefs whip up dishes like grilled mahi-mahi, veal, and possibly the best grilled lobster you’ll ever have. .
On this island, it can be difficult to stand out for food, but Uchu captivates even the biggest eaters with its creativity in Peruvian cuisine. Enjoy the very distinct flavors of the Andes, the jungle and the Peruvian coast, while overlooking the beautiful cove of Cap Juluca. Don’t miss the fresh ceviches and the tropical Punch Pisco Anguilla-meets-Peruvian.
Traditional sailing boat
There’s something magical about this classic West Indian Sloop, led by First Mate and chef Deborah Vos and Captain Laurie Gumbs, who have their roots in Anguilla for generations. Book their sunset tour if you want to sip champagne cocktails and drink rum while exploring the beautiful Anguillan coastline and sunsets. (Let’s be honest, ai are not?)
This vibrant outdoor bar at the Four Seasons offers a trendy LA vibe thanks to a mix of expert baristas, creative sushi, and custom Cuban cigars. But it’s the amazing sunset views that will leave you in awe, hence the name.
Located inside the one-of-a-kind gem of the Malliouhana hotel, this bar matches the Hollywood Regency vibe. Design details include birdcage candle holders, jungle-themed artwork and lots of palm leaf print pillows. The cliff-side perch is the place to go for Caribbean tacos and classic rum drinks.
Cap Juluca, A Belmond Hotel
It just doesn’t get sexier than this. Guests stay in whitewashed Moorish villas decorated with sculptural furniture and gorgeous tiles, overlooking a beach so perfect it looks permanently Instagram-filtered. Cipriani Cip’s delicious sister restaurant sits at one end of the beach, while a chic beach shack beckons to strong Sundays at the other.
Zemi Beach House
Ask anyone from Anguilla which beach is their favorite (a frequent island debate), and Shoal Bay East is frequently cut. Zemi is the only resort on this spectacular mile-long beach. Highlights include lounging on a palm-lined pool lounger, tasting their 100+ different varietals, and enjoying Eastern and Western wellness treatments at the Thai house spa. their magic. It sounds terrible, we know.
Aurora Anguilla Resort & Golf Club
This 300-acre property is set up like two resorts in one — each with guestrooms, pools, restaurants, great staff, and a beach. We’re part of the Rendezvous Bay side with its impossibly stunning beachfront villas and luxurious poolside setting (complete with rose snaps every afternoon). The hotel is a foodie destination with seven distinctive locally sourced restaurants, including the island’s first steakhouse.