How to describe Anguilla? The dreamy 16-mile-long Caribbean island is quite literally what vacation dreams are made of, particularly for foodies, design junkies, and beach lovers who head to this quiet, uncrowded island for the robust food scene, stunning boutique hotels, and 33 (!) picturesque white sand beaches. Did we mention flights start at $135? If you’re ready to book your ticket, here’s our guide to where you can stay, eat, drink, etc.
AXA Hike Life
Want to see a side of Anguilla you would probably never discover 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, and scenic trails, and secret beaches. Start brainstorming captions now.
Calypso Charters Anguilla
Whether you’re down for reeling in some mahi-mahi, snorkeling in a secluded turquoise cove, exploring one of Anguilla’s uninhabited outer islands, or sadly need a shuttle back to St. Maarten to catch your flight—Calypso Charters’ fleet of power boats and skilled captains is at the ready.
It’s hard to choose from 33 options, all of which are open to the public and most feature awesome beach shacks. Our favorite spots for a lunch/beach doubleheader are Blanchards on Meads Bay, Nat’s Place on the windswept 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 eatery to open one of the island’s best globally-inspired restaurants. Chef Carrie’s take on red snapper, rack of lamb, and lobster fritters is not to be missed. Late night, head downstairs to the Moroccan cocktail lounge for live music and killer cocktails.
This off-the-beaten-path, laid-back beach shack in Island Harbor is worth the trek. Owner and fisherman Warren “Mutt” Webster reels in 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 food-wise, but Uchu captivates even the most jaded eater with its creative take on Peruvian cuisine. Enjoy the very distinct flavors of the Andes region, jungle, and the Peruvian coast, while overlooking Cap Juluca’s scenic cove. Don’t miss the fresh ceviches and tropical Anguilla-meets-Peru Pisco Punch.
There is something incredibly magical about this classic West Indian Sloop, led by First Mate and chef Deborah Vos and Captain Laurie Gumbs, whose roots go back generations in Anguilla. Book their sunset sail if you feel like sipping on champagne cocktails and rum punch while checking out the beautiful Anguillan coastline and sunset. (Let’s be real, who doesn’t?)
This dazzling open-air bar at the Four Seasons has a very trendy L.A. vibe thanks to the combo of expert mixologists, creative sushi, and Cuban cigars available on request. But it is the unparalleled sunset views that will leave you awestruck, hence the name.
Located inside the one-of-a-kind gem of a hotel Malliouhana, this bar matches its Hollywood Regency vibes. Design details include birdcage candleholders, jungle-themed artwork, and plenty of palm-leaf printed pillows. The cliffside perch is the spot to nosh on 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 decked out with sculptural furniture and gorgeous tilework, overlooking a beach so perfect it looks permanently Instagram-filtered. Cipriani’s delicious sister restaurant Cip’s is on one end of the beach, while a chic beach shack beckons with strong Sundowners on the other.
Zemi Beach House
Ask anyone from Anguilla which beach is their favorite (a frequent island debate), and Shoal Bay East frequently makes the cut. Zemi is the only resort on this breathtaking mile-long beach. Highlights include lounging on a poolside daybed shaded by palm trees, sampling their 100-plus varieties of small batch rums, and indulging in the East-meets-West wellness therapies at their magical Thai house spa. Sounds terrible, we know.
Aurora Anguilla Resort & Golf Club
This expansive 300-acre property is set up like two resorts in one—each with its own guest rooms, pool, restaurants, amazing staff, and beach. We’re partial to the Rendezvous Bay side with impossibly gorgeous beachfront villas and chic poolside scene (complete with rosé spritzer shots each afternoon). The hotel is a culinary destination unto itself with seven exceptional locally sourced restaurants, including the island’s first steakhouse.