How to describe Anguilla? The dreamy 16-mile-long Caribbean island is literally what vacation dreams are made of, especially for foodies, design junkies and beach lovers who head to this quiet, uncrowded island for the scene. robust gastronomy, stunning boutique hotels and 33 (!) picturesque white sand beaches. Did we mention flights starting at $135? If you’re ready to book your ticket, here’s our guide to where you can stay, eat, drink, and more.
AXA Hiking Life
Want to see a side of Anguilla that you’ll probably never experience on your own? Book an adventure with AXA Hike Life (just DM them on Instagram). Their intrepid guides will lead you through Anguilla’s incredible rainforests, caves, cliffs, scenic trails and secret beaches. Start thinking about captions now.
Calypso Charters Anguilla
Whether you want to relax in mahi-mahi, snorkel in a secluded turquoise cove, explore one of Anguilla’s uninhabited outer islands, or unfortunately need a shuttle to return to St. Maarten to catch your flight, Calypso Charters fleet of motorboats and qualified captains are ready.
It’s hard to choose from 33 options, all of which are open to the public and most feature great beach cabanas. Our favorite spots for a lunch/beach double-blind are Blanchards on Meads Bay, Nat’s Place on windswept and secluded 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 restaurant to open one of the island’s top globally-inspired restaurants. Chef Carrie’s red snapper, rack of lamb and lobster fritters are not to be missed. Late at night, descend on the Moroccan cocktail bar for live music and mind-blowing cocktails.
This off-the-beaten-path, laid-back beach hut in Island Harbor is worth a visit. Owner and fisherman Warren “Mutt” Webster takes care of the daily catch while the chefs work their magic on dishes like grilled mahi-mahi, calamari and possibly the best grilled lobster you’ve ever had.
On this island, it can be hard to stand out culinaryly, but Uchu captivates even the most jaded eaters with his creative take on Peruvian cuisine. Enjoy the very distinct flavors of the Andes region, the jungle and the Peruvian coast, while overlooking the picturesque cove of Cap Juluca. Don’t miss the fresh ceviches and tropical Anguilla-meets-Peru Pisco punch.
There’s something incredibly magical about this classic West Indian sloop, helmed by First Mate and Chief Deborah Vos and Captain Laurie Gumbs, whose roots go back generations to Anguilla. Book their sunset sail if you fancy sipping champagne cocktails and a rum punch while taking in the stunning Anguillan coastline and sunset. (Let’s be real, who doesn’t?)
This dazzling outdoor bar at the Four Seasons has a very hip LA vibe thanks to the combination of expert mixologists, creative sushi and Cuban cigars available on request. But it’s the incomparable sunsets that will leave you speechless, hence its name.
Located inside the one-of-a-kind gem of a Malliouhana hotel, this bar matches its Hollywood Regency vibe. Design details include birdcage-shaped candle holders, jungle-themed artwork, and plenty of palm-leaf print pillows. The cliffside perch is the perfect place to sample Caribbean tacos and vintage rum drinks.
Cap Juluca, a Belmond Hotel
It just doesn’t get more glamorous than this. Guests stay in whitewashed Moorish-style villas adorned with sculptural furnishings and beautiful tiles, overlooking a beach so picture-perfect it seems permanently Instagram filtered. Cipriani’s delicious sister restaurant, Cip’s, sits at one end of the beach, while a chic beach shack awaits with mighty sunsets on the other.
Zemi Beach House
Ask anyone in Anguilla which beach is their favorite (a frequent debate on the island), and Shoal Bay East often makes the cut. Zemi is the only resort on this breathtaking one kilometer long beach. Highlights include lounging on a daybed by the pool under the shade of palm trees, sampling their over 100 varieties of small-batch rums, and indulging in East-meets-West wellness therapies in their magical Thai House spa. It sounds terrible, we know.
Aurora Anguilla Resort & Golf Club
This sprawling 300-acre property is laid out as two resorts in one, each with its own rooms, pool, restaurants, exceptional staff, and beach. We’re partial to the Rendezvous Bay side with impossibly gorgeous beachfront villas and a chic poolside scene (complete with rosy spritzer shots every afternoon). The hotel is a culinary destination unto itself with seven outstanding local restaurants, including the island’s first steakhouse.