Despite its small size, Anguilla has around 70 restaurants: stylish temples of haute cuisine; classic, barefoot beachfront grills; roadside barbecue stands; food vans; and casual cafés. Many have breeze-swept terraces for dining under the stars. Call ahead—in winter to make a reservation and in late summer and fall to confirm whether the place is open. Anguillian restaurant meals are leisurely events, and service often has a relaxed pace, so settle in and enjoy. Most restaurant owners are actively and conspicuously present, especially at dinner.
What to Wear: During the day, casual clothes are widely accepted: shorts will be fine, but don't wear bathing suits and cover-ups unless you're at a beach bar. In the evening, shorts are okay at the extremely casual eateries. Elsewhere, women wear sundresses or nice casual slacks; men will be fine in short-sleeve shirts and casual pants or nice shorts. Some hotel restaurants are slightly more formal, but that just means long pants for men.