Day 1

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.