Edgartown

Once a well-to-do whaling center, Edgartown remains the Vineyard's toniest town and has preserved great parts of its elegant past. Sea captains' houses from the 18th and 19th centuries, ensconced in well-manicured gardens and lawns, line the streets. You could wander for hours studying the architecture and marveling at the meticulously restored structures. Plenty of shops as well as sights and other activities occupy the crowds who walk the streets in summer. There's a healthy balance of sophistication and small-town local flavor here.