Edgartown

Edgartown is the postcard. White clapboard captains’ houses line tight streets that lead to a working harbor; the lighthouse anchors a small beach in the middle of town; the Chappy Ferry shuttles cars across to Chappaquiddick on a one-minute crossing that’s become a sightseeing line of its own. Most of the island’s fine-dining restaurants cluster here, and the village core is genuinely walkable. South Beach (Katama) is the surf beach at the bottom of Katama Road; Fuller Street and Lighthouse cover the protected-water side.