Lay of the Land
At just 100 square miles, the Vineyard is split between down-island and up-island towns.
Edgartown: Stately homes of 18th-century whaling captains line the streets of this historic town.
Oak Bluffs: Known for its Victorian cottages and kitschy fudge shops, this is the island’s tourist hub.
Vineyard Haven: Come here for one-off boutiques and the main ferry terminal.
Aquinnah: Make the trek to this western town for its colorful clay cliffs and Gay Head Lighthouse.
Chilmark: Islanders escape the summer crowds for the quiet fishing villages along Chilmark’s coastline.
West Tisbury: The most bucolic area has acres of rolling farmland.
Catch a ferry from Massachusetts, New York, or Rhode Island. If you don’t bring your car, rent a bicycle or a moped. Taxis are also plentiful.