Once a well-to-do whaling center, Edgartown remains the Vineyard's toniest town and has preserved parts of its elegant past. Sea captains' houses from the 18th and 19th centuries, with well-manicured gardens and lawns, line the streets.
A sparsely populated area with many nature preserves, where you can fish, Chappaquiddick Island, 1 mile southeast of Edgartown, makes for a pleasant day trip or bike ride on a sunny day. The "island" is actually connected to the Vineyard by a long sand spit that begins in South Beach in Katama. It's a spectacular 2¾-mile walk, or you can take the ferry, which departs about every five minutes.
On the island's Mytoi preserve, a boardwalk runs through part of the grounds, where you're apt to see box turtles and hear the sounds of songbirds. Elsewhere you can fish, sunbathe, or even dip into the surf; use caution, as the currents are strong.