How to Have a 3-Day Weekend Getaway in Anguilla

Editor’s Note: Some of the information below may be out-of-date. Anguilla was heavily impacted by Hurricane Irma. Please visit caribbeantravelupdate.com or the specific hotel’s website for updates.

It's all about Anguilla's beaches — a whopping 33 of them — on an island that measures just 16 miles long and 3 miles across (at its widest point). That idyllic combination of sugar-white sand and uber-blue water can be found wherever you go on Anguilla island, but most visitors head to what's considered one the world's top beaches, Shoal Bay East. The island also takes top marks in cuisine — and boasts some of the Caribbean's best-loved resorts. Here's how to spend 36 hours on this laid-back Leeward Island.

Anguilla Beaches: Shoal Bay East
Shoal Bay EastShutterstock

Day One

Hit the beach: Pop by for a brioche and a strong espresso at Cafe de Paris near the West End Village. Then continue to the famed Shoal Bay East to stake out your slice of sandy heaven. (All Anguilla beaches have public access and are free.) This is one of the busiest beaches; day-trippers come via ferry from nearby St. Martin, and people flock to the restaurants and bars that line the shore. Not to worry: On this 2-mile stretch of sand, you're bound to find a secluded spot.

Anguilla Resorts: Viceroy Anguilla
The Sunset Lounge at Viceroy AnguillaCourtesy Viceroy Anguilla

Cocktail Hour: Bid the day farewell — with a potent Painkiller in hand — at the aptly named Sunset Lounge at Viceroy Anguilla. Arrive on the early side to score a primo table at the open-air bar; you'll be rewarded with a vivid red, yellow and orange Caribbean sky as the sun sinks into Barnes Bay.

Anguilla Island: SandBar
Drinks with a view at SandBarZach Stovall

Go Bar-Hopping: The site of Anguilla's main harbor, Sandy Ground is an easily walkable village filled with bars, restaurants and late-night music venues. Chill out at SandBar, which serves inventive (and affordable) tapas in a casual beachfront setting, or honor the island's British heritage at Ripples, with English pub-style fare.

Anguilla Island: Nightlife at the Pumphouse
The scene at The PumphouseZach Stovall

Dance the night away: Live music is a must-do in Anguilla, and the quirkiest spot to see it is The Pumphouse, a former salt factory with wood walls and rafters lined with funky memorabilia. Bands take the stage every night, starting around 9:30, but Thursdays, this is the place to be. See how to make the infamous Pumphouse Rum Punch.

Anguilla Beaches: Scilly Cay
A lobster lunch on Scilly CayZach Stovall

Day Two

Offshore Escape: If it's Wednesday or Sunday, make a day of it on Scilly Cay. At the fishing village of Island Harbour, a (free) boat picks you up from the pier and spirits you to this private spit of land for a day of snorkeling (bring your own gear), grilled local lobster and crayfish, stiff "rhum punch" and live reggae (Sundays only). The fun ends at 5 p.m. — there's no electricity on the tiny isle.

Anguilla Island: Smokey's at the Cove
Smokey's at the CoveZach Stovall

Barbecue and Bands: A visit to Anguilla isn't complete without trying the island's famed barbecue. There are beachfront joints (Garvey's Sunshine Shack) and road-side stands (Ken's Pork) but Smokey's at the Cove is a true local institution. Chow down on ribs and chicken under a beach from tent while musicians — including Omari Banks, song of Anguillan reggae star Bankie Banx — flaunt their talent daily.

Anguilla Beaches: Little Bay
Little BayZach Stovall

Day Three

Time to Climb: Skip the pricey hotel breakfast and fuel up with a hearty bacon, egg and cheese sandwich at Valley Bistro. You'll need some fortification for the journey to the remote snorkeling haven of Little Bay. Getting to the minuscule beach involves hiking an unmarked trail then climbing down a steep cliff with a rope as your only safety net. Afraid of heights? There are usually local boaters who will pick you up at nearby Crocus Bay and speed you over for around $15.

Anguilla Island: Restaurant at Malliouhana
Gourmet pizza at the Restaurant at MalliouhanaCourtesy Restaurant at Malliouhana

Lunch With a View: Perched on a bluff overlooking Meads Bay, the Restaurant at Malliouhana has a new menu featuring gourmet pizza, locally caught snapper, and sinful lobster mac 'n' cheese, along with super-healthy vegetarian options like grilled kale with local fresh corn "funghi."

Anguilla Resorts: CuisinArt Golf Resort & Spa
CuisinArt Golf Resort & SpaZach Stovall

Gourmet Gastronomy: Not much farming happens in Anguilla with its thin soil and scant water, so the folks at CuisinArt Golf Resort & Spa built an onsite hydroponic farm to supply fresh produce and herbs to all its restaurants. Get a taste of that goodness at the eight-course Wednesday night Chef's Table, with creative local fish and seafood dishes.