You can people watch at lovely Shoal Bay, or make your way to Little Bay, where dramatic cliffs line a small gem of a beach. The sand is more gray than white, and it takes some effort to get there – a rope and a net ladder make the hike down and up the cliff a bit easier – unless you arrive by boat. The bay is protected as a marine park, so swimming and snorkeling are joys, and the bird life can keep you happily distracted for hours.
Anguilla’s national pastime makes for a great spectator sport. The sailboat-racing season runs from May through August, and during that time you can join the locals, first at cliffside vantage points to watch prized craft compete offshore, then at the post-race parties that carry on well into the night.
Kick back with a fresh-from-the-sea grilled lobster at a beachside shack, or dress up for lobster crepes in an elegant “Euro-Caribbean” restaurant that combines continental and West Indian cuisines; Anguillan pea soup is a local favorite. Wine lovers take note: The famed Malliouhana Restaurant at Meads Bay has a 25,000-bottle wine cellar.