If you know you’ll be in need of a winter getaway as soon as the holiday season has passed, then Anguilla should be on your radar.

 Less visited than some of its neighboring islands but no less beautiful, Anguilla embodies the very best of the Caribbean minus the crowds (no wonder it’s popular with the A-list and has a 75% repeat visitor rate). From its idyllic cays surrounded by aquamarine water to its warm and welcoming hospitality –– and, of course, notable golf courses –– Anguilla is an incomparable Caribbean paradise that should definitely be on your radar. And with American Airlines expanding its direct service from Miami to Anguilla from now until March, it’s more convenient than ever to make the trip.

Experience the Island’s Lauded Golf Courses

After a fresh redesign that solidified its reputation as one of the Caribbean’s top golf courses, Aurora Anguilla’s Greg Norman Signature Design Championship Course reopened in the spring of 2022. With a stunning backdrop of Rendezvous Bay and distant views of St. Maarten, the 18-hole course blends unforgettable aesthetics with ultimate playability and all the post-game conveniences you could need, including recovery therapies and a full-service restaurant.

Explore paradisiacal Cays

A short boat ride off the shore of Anguilla’s main island you’ll find a series of small cays –– pristine islets perfect for afternoons spent swimming, snorkeling, sun bathing, dabbling in watersports, and bird watching (Scrub Island alone boasts 34 different species). Three of the cays –– Prickly Pear, Sandy Island, and Scilly Cay –– have restaurants where you can feast on the freshest seafood imaginable (think: grilled lobster and just-caught fish), while sipping rum punch and making new friends as live music plays.

Scuba dive at a shipwreck

The island has dozens of dive sites under the protection of seven marine parks, and is well-known among seasoned divers for its shipwrecks; eight sunken vessels offer underwater adventure and encounters with abundant marine life, from sharks and rays to turtles and angelfish.

Take a sublime sunset sailing trip

Watching a tangerine sunset from the deck of a sailboat, Champagne cocktail in-hand and sea breeze in your hair, is a quintessential Anguilla vacation experience. A main feature is a 2.5 hour trip along the coastline, savoring ocean vistas, boozy drinks, and house-made hors d’oeuvres as golden hour turns to dusk. If you’re lucky you might even catch a glimpse of the “green flash,” an optical illusion occurring at sunset when refracted light creates an emerald green glow just as the sun sinks beneath the horizon.

Adventure with a local

Immerse yourself in Anguillian culture and try something new when you book an adventure with Quest Experiences. Quest’s local expert guides offer specialty tours including hiking and caving, night and day kayaking, shore fishing, scuba diving, kite making and more. Unique offerings like salt picking offer insights into the history of the island while providing you with an only-in-Anguilla experience to cherish.

Sample Anguilla’s dining and after-dark scenes

The island’s eclectic dining scene runs the gamut from elevated fare at places like ​​Veya (an upscale establishment where Caribbean dishes are mixed with North African and Southeast Asian influences) or Blanchards Restaurant (an ocean-side venue with an award-winning wine list), to casual cuisine at buzzy spots including Sunshine Shack (a laid-back beach bar serving BBQ on the sand) and Vincy on the Beach (a locally owned restaurant with Anguillian dishes). For a nightcap – or an evening spent dancing under the stars – head to the Lit Lounge (a two-level bar with DJ and musical performances spanning all genres) or Elvis’ (a beachy hangout with hammocks, live music and feisty cocktails).