Spanning a mere 35 square miles, intimate Anguilla is home to the white sand beaches and turquoise waters that fairytale vacations are made of.
A recently introduced nonstop flight out of BWI makes this islet east of Puerto Rico and the Virgin Islands relatively quick and easy to reach, even if only for a long weekend. Fares on AnguillAir start as low as $329 one-way, with flights offered every Monday and Friday.
As the northernmost island of the Lesser Antilles, the British territory (reminder: bring your passport) enjoys trade wind breezes year-round, and in early summer, a lull in tourism prompts discounts on hotel bookings. Vacation packages through Anguilla Air Holidays, for example, offer savings of up to 20% off listed hotel rates. Just keep in mind that many resorts close in late August through September when hurricane season kicks into full swing.
Where to Eat & Drink
Dining options abound on the island, from high-end chef’s tasting menus to barefoot-on-the-beach happy hours. For a thorough sampling of its ocean bounty, visit during the annual Anguilla Culinary Experience, a five-day food and wine festival happening May 13-17 this year. Participating restaurants include Salt, a seafood-forward spot turning out mainstays such as roasted pumpkin soup, spiny lobster, oxtail croquettes and fresh fish with Caribbean spices. Many of chef Manu Calderon’s dishes are seasoned in citrus and cooked over an open flame for a smoky finish.
At the Straw Hat, a beachfront bar and restaurant where shoes and shirts are optional, park yourself on a lounger and order the ti’ punch, a French Caribbean concoction (think of it as the daiquiri’s more potent cousin) blending rum, lime juice, cane syrup and bitters. A food menu offering bold West Indies fare from sunrise to sunset finds choices like lobster Johnny cake Benedict, big-eye tuna flatbread and conch potstickers.
No visit to Anguilla is complete without a slice of Blanchards’ ultimate carrot cake, a towering six-layer treat interspersed with lemon curd and raspberry puree and topped with shaved coconut. The restaurant’s beach shack is a hopping spot for takeout, while the elegantly shuttered, open-air dining room is known for its family-style Caribbean Sampler of grilled crayfish, jerk chicken and salmon Provencal. Blanchards also boasts one of the most extensive wine and spirits lists on the island, with more than 300 bottles of vino and 200 kinds of rum, but who’s counting?
Where to Stay
Anguilla’s vibrant west side, roughly a 20-minute taxi ride from the airport, is home to five-star resorts such as the extravagant Cap Juluca, where crisp white Greco-Moorish colonnades frame views of the water.
The reliably posh Four Seasons Resort blends sleek architecture with natural furnishings such as driftwood lamps and petrified-wood tables. Both resorts offer private beaches, luxury spa amenities, infinity pools overlooking the ocean and a host of excursions, from sailing and fishing charters to sunset cruises.
Wallet-friendlier boutique hotels such as the Frangipani Beach Resort and the Aurora Anguilla Resort & Golf Club also offer poolside and oceanfront lounging, a host of water excursions, and family-friendly lodging, including suites with pull-out sleeper sofas and kitchenettes. Frangipani provides complimentary beach cruiser bicycles, and Aurora has an adjacent waterpark that’s popular with kids.
Where to Play
Tempting as it may be to plant yourself in one spot to decompress with a beach read, Anguilla offers plenty of enticing land and sea adventures. At Prickly Pear cays, two uninhabited islands divided by a narrow channel, you can pop on a snorkel and fins from the beach and swim out to protected coral reefs teeming with tropical fish. Book a reservation ahead of time at beachfront barbecue Prickly Pear Restaurant and your 20-minute boat ferry to the cays, leaving from of the tiny village of Sandy Ground, is included in the cost of your meal.
Anguilla has 33 unique beaches, including the supremely strollable Rendezvous Bay; rocky Captain’s Bay, home to a heart-shaped tidal pool; and Shoal Bay East, known for its powdery pink sand. Explore these and other island wonders by renting a Moke, a vehicle that looks like a cross between a Jeep and a golf cart. Available in an array of fun colors with manual or automatic transmission, these British beach buggies seat up to four passengers.
Want a taste of continental Europe? Island hop by way of the Blowing Point Ferry ($30 one-way, plus port tax) to neighboring Saint Martin. The north end, or “French side,” as it’s known to locals, boasts Parisian bakeries, wine bars and fashion boutiques, while the southern “Dutch side” offers the advantage of duty-free shopping, thanks to its 1939 designation as a free port. Fair warning: You might need a bigger suitcase for that souvenir haul.