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 the 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 Oprah Winfrey, Carly Simon, Ted Danson, Spike Lee, and Diane Sawyer; former president Barack Obama and his family vacationed here nearly every summer of his two terms in the Oval Office. 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.