Martha's Vineyard

Martha's Vineyard, a Massachusetts island, sits in the Atlantic just south of Cape Cod. A longtime New England summer colony, it encompasses harbor towns and lighthouses, sandy beaches, and farmland. It's accessible only by boat or air. Vineyard Haven, on the eastern end, is a ferry port and the island's commercial center. Oak Bluffs has Carpenter Gothic cottages and an iconic carousel.

The triangle-shaped island – sitting about 8 miles off the coast of Cape Cod, Massachusetts – has been a secret summer hideaway of the rich and famous for more than a century. Today, the "Hollywood East" reputation is going strong thanks to frequent visitors like former President Barack Obama, David Letterman, and Bill Murray, among many others. But despite the all-star summer lineup, a laid-back lifestyle rules the island.

The main draw of rushing Vineyard visitors off the ferry is the chance to let their hair down for a long weekend. You'll find insanely expensive summer cottages and pricey restaurants in some corners of the island like Chilmark. But low-key towns and villages like Vineyard Haven and Menemsha are still predominantly focused on their marine industries and offer a more casual experience. Even the island's must-have souvenir – a Black Dog sweatshirt – is informal. So swap the stilettos for your scrappiest flat sandals, and do play it cool when you spy some film stars in Edgartown; everyone deserves a slice of a Vineyard vacation.

Address: Dukes County, Massachusetts