Far less developed than Cape Cod—thanks to a few local conservation organizations—yet more cosmopolitan than neighboring Nantucket, Martha's Vineyard is an island with a double life. From Memorial Day through Labor Day the quieter (some might say real) Vineyard quickens into a vibrant, star-studded place.
The busy main port, Vineyard Haven, welcomes day-trippers fresh off ferries and private yachts to browse in its array of shops. Oak Bluffs, where pizza and ice cream emporiums reign supreme, has the air of a Victorian boardwalk. Edgartown is flooded with seekers of chic who wander tiny streets that hold boutiques, stately whaling captains' homes, and charming inns.
Summer regulars have included a host of celebrities over the years, among them Carly Simon, Ted Danson, Spike Lee, and Diane Sawyer. If you're planning to stay overnight on a summer weekend, be sure to make reservations well in advance; spring is not too early. Things stay busy on September and October weekends, a favorite time for weddings, but begin to slow down soon after. In many ways the Vineyard's off-season persona is even more appealing than its summer self, with more time to linger over pastoral and ocean vistas, free from the throngs of cars, bicycles, and mopeds.
Except for Oak Bluffs and Edgartown, the Vineyard is "dry," but many restaurants allow you to bring your own beer or wine. The town of Vineyard Haven has recently allowed beer and wine—but no liquor—to be sold in restaurants only.