Anguillan residents call themselves “Belongers.” Here’s how to become one.
Check-In: Modernists stay atop a bluff at the new Viceroy Anguilla (doubles from $695) with 166 teak-and-cream rooms that have private decks and plunge pools. A more traditional option is the 179-acre Cap Juluca (doubles from $425, including breakfast), which underwent a $22 million renovation two years ago. All 98 rooms, now with Frette linens and Moroccan-style rugs, line a calm bay.
Lunch: Borrow one of the Viceroy’s trail bikes and pedal to the open-air Straw Hat Restaurant (lunch for two $70), famous for its grilled Anguillan crayfish drizzled with ginger vinaigrette.
Music: While away the afternoon with a Pyrat rum piña colada at Dune Preserve (drinks for two $15), a driftwood bar owned by Anguilla-born reggae artist and raconteur Bankie Banx.
Dinner: On an island with dozens of roadside grill stands, the local standout is B&D’s Barbecue (dinner for two $25) for its smoky pork ribs to go. If you’d rather linger over West Indian dishes (Creole conch stew with fried plantains; goat curry), grab a table at E’s Oven (dinner for two $100). Chef Vernon Hughes cooks on the same spot where his mother presided over her stone furnace.
Drinks: Rum punches and reggae bands are the draw at the Pumphouse (drinks for two $16). Get there early on Thursdays; calypso night draws the crowds.
Breakfast: French expat Geraud Lavest oversees the kitchen at Geraud’s Patisserie (breakfast for two $24) where the café au lait is straight out of Paris but the mango-topped French toast has a tropical spin. In October, you’ll find Lavest bottling house-made peach-ginger marmalade. The jars ($8) will also pack neatly in your suitcase.
Beach: Anguilla has 33 beaches with sand that ranges from pink to vanilla and shallow bays well-suited for snorkeling. Bring fins and a mask to gin-colored Crocus Bay to spot angelfish. Then head down the beach to designer Fabiana Liburd’s boutique Why Knot. Ask her to show you how to tie her signature cover-up in the local style.
Lunch: On weekends, chicken barbecue, complete with Carib lagers and live music near the surf, is the main attraction at Smokey’s at the Cove (lunch for two $60).
Spa: CuisinArt Resort & Spa (doubles from $815) has the largest spa and fitness center on the island. Choose the cucumber and aloe wrap ($120): this hydrating treatment uses products from the resort’s hydroponic farm.
Dinner: Don’t leave Anguilla without an evening at KoalKeel (dinner for two $130), which is set in a limestone cottage built in the 18th century by Dutch sugarcane planters. Chef Gwendolyn Smith’s menu includes crayfish ravioli, pigeon-pea soup, lamb medallions with pumpkin gratin, and—for a sweet finale—the rum truffle tower.