Odds are, this ferry-port town – where the lion's share of summer day-tripping boats arrive – will be your introduction to the island. Welcome to the Vineyard's summer fun mecca: a place to wander with an ice-cream cone in hand, poke around honky-tonk sights and go clubbing at night.
The western side of the island – known as Up Island and comprising the towns of West Tisbury, Chilmark and Aquinnah – is a patchwork of rolling hills, small farms and open fields frequented by wild turkeys and deer. Soak up the scenery, take a hike, pop into a gallery, stop at a farm stand; munch, lunch and beach.
Although it's the island's commercial center, Vineyard Haven is a town of considerable charm. Its harbor has more traditional wooden schooners and sloops than any harbor of its size in New England. Central Vineyard Haven (aka Tisbury) is just four or five blocks wide and about a half-mile long.
Chilmark & Menemsha
Occupying most of the western side of the island between Vineyard Sound and the Atlantic, Chilmark is a place of pastoral landscapes and easygoing people. Chilmark's chief destination is the picture-perfect fishing village of Menemsha, where you'll find shacks selling seafood fresh off the boat.