Everything that can taint your Caribbean vacation—high-rise chain hotels, Euro-trash casinos, overrated and overcrowded beaches—has been banished in Anguilla. This tiny, perfect island of just 100 square kilometres has a staggering 33 vanilla (rhymes with Anguilla, which means eel) sand beaches. Best of all, its just-hard-enough-to-reach location and steep prices keep those beaches sparsely populated and the level of authenticity high; there are just six traffic lights on the island, license plates have just three digits and the locals are genuinely happy to meet you.

Stay
Villas are the accommodation of choice here. If you can have your own kitchen, private gym, infinity plunge pool, helipad and room for all your friends, why wouldn’t you? We stayed at Meads Bay Beach Villas: luxe two-bedroom suites (from $700 a night) with full kitchens—we had the fridge pre-stocked with Corona and Diet Coke—and private plunge pools. The beach is a few steps away (264-497-0271, meadsbaybeachvillas.com). The over-the-top Sheriva is a cluster of oceanfront “super villas” with a total of 20 bedrooms and seven pools—rent one villa (from $1,700 a night in winter) or do the whole compound (264-498-9898, sheriva.com).

Eat
Carrie and Jerry Bogar ran the acclaimed Empire restaurant in central Pennsylvania before relocating to Anguilla to open Veya: Cuisine of the Sun (264-498-8392, veya-axa.com) last year. Carrie, a Culinary Institute of America-trained chef, has married her chic contemporary cooking with tropical ingredients: Dishes like grilled watermelon and poached shrimp salad with spiced pecans and vanilla-cured duck with guavaberry sauce will rock your palate. Jerry is a gracious host who keeps the inventive cocktails (like the Sandy Ground: Ruby Red vodka, raspberry and lime) and conversation flowing.

Tasty’s (264-497-2737) looks like a humble café but houses the upscale talent of chef Dale Carty, who trained in France while working for the luxe Malliouhana resort but now dishes up toasty lobster bisque and delicious warm seafood salads to appreciative diners. But to really eat like the locals do, line up at the lunch trucks that cluster in the Valley, Anguilla’s downtown area. The favourite is Hungry’s Good Food, which is especially known for its soups: goat, conch, bull foot or pig tail broths might be simmering. Every Easter weekend, the Festival del Mar held at Anguilla’s Island Harbour celebrates the freshest sea treats and local specialties.

Drink
The Dune Preserve (Rendezvous Bay, 264-772-9259, bankiebanx.net), the habitat of local folk-reggae star Bankie Banx, is like a ramshackle Gilligan’s Island, with chunks of lumber and random boat parts cobbled together into a bar, restaurant and live music venue. Try a glass of Doonshine, a wicked ginger-and-rum potion, at your own risk.

Myra’s Mango BBC (mango juice, Baileys, banana and coconut, with fresh nutmeg and a float of rum), served by the beautiful and charming Myra Richard at Kuyah (264-497-2011, ku-anguilla.com) beach bar at Kú resort, is the best tropical drink you’ll ever taste.

Do
The Greek-inspired villas of Temenos flash as brightly as a set of Hollywood teeth. Temenos Golf Club (264-498-7000, temenosgolfclub.com), the creation of pioneering local hoteliers Bob and Melinda Blanchard (authors of A Trip to the Beach, a must-read for those thinking of defecting here), is Anguilla’s only course, so it’s a good thing they got it just perfect. Designed by Greg Norman, the layout tops at a very non-resorty 7,100 yards, but the more approachable forward tees allow for a civilized round with plenty of opportunity to take in the spectacular azure vistas.

CuisinArt Resort and Spa (800-943-3210, cuisinartresort.com)—yes, that Cuisinart—is home to not only Santorini Restaurant, with its 3,600-bottle wine cellar and the world-ranked Venus Spa, but also to the West’s own Dr. Howard Resh. The former UBC graduate and professor now minds the world’s first resort-based hydroponic farm, 18,000 square feet of luscious lettuces, herbs, tomatoes, peppers, cucumbers and edible flowers. He gives tours Mondays, Thursdays and Saturdays at 11 a.m.

For just $25 a person the Anguilla National Trust (265-497-5297, axanationaltrust.org) will arrange custom tours of the conservation area and protected sites it manages for birdwatchers, history nuts and others. Rare bird species on the island include the white-cheeked pintail, snowy egret, lesser yellowlegs and the endangered Caribbean coot. Petroglyphs as old as 1,500 years are a highlight of the Big Springs Heritage Site.

Getting There
Connect from Puerto Rico’s San Juan Airport to Anguilla on American Eagle. If you fly into St. Maarten on Continental, US Airways, Delta or American, take the quick Funtime Charters (264-235-8106, funtimeai.com) $70 ferry service from Marigot Bay to Anguilla’s Blowing Point. Anguilla package holidays are available from Air Canada Vacations and Total Vacations through travel agents.

Live
The new Kelly Werstler-designed Viceroy Anguilla (264-497-0757, viceroyanguilla.com) has villas and townhomes from $900,000 (U.S.). This summer the Temenos Residences (264-498-7000, temenosanguilla.com) open, with 18 estate homes, 10 villas and 38 spa-villas from $1,500,000 (U.S.). Shoal Bay (264-497-7462, ownshoalbay.com) has green condos from $700,000 (U.S.)—a bargain, only in Anguilla.