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Despite its small size, Anguilla has around 70 restaurants: stylish temples of haute cuisine; classic, barefoot beachfront grills; roadside barbecue stands; food carts; 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 you've chosen is even open at that time. Anguillian
Anguillian restaurant meals are leisurely events, and service is often at a relaxed pace, so settle in and enjoy. Most restaurant owners are actively and conspicuously present, especially at dinner. It's a special treat to take the time to get to know them a bit when they stop by your table to make sure you are enjoying your meal.
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. Some hotel restaurants are slightly more formal, but that just means long pants for men.