The island is roughly triangular, with maximum distances of about 20 miles east to west and 10 miles north to south. The west end of the Vineyard, known as Up-Island—from the nautical expression of going "up" in degrees of longitude as you sail west—is more rural and wild than the eastern Down-Island end, comprising Vineyard Haven, Oak Bluffs, and Edgartown.
Vineyard Haven (Tisbury). One of the island's busiest towns, Vineyard Haven sees ferry traffic all year long. A fairly compact downtown area keeps most shopping and dining options within easy reach.
Oak Bluffs. Once a Methodist campground, Oak Bluffs is a little less refined than the other towns. It has a vibrant vacation vibe, with lots of nightlife, dining, and shopping.
Edgartown. Dominated by the impeccably kept homes of 19th-century sea captains, Edgartown has a sense of sophistication. There's great history here, and several museums tell the story.
Chappaquiddick Island. Take the tiny ferry from Edgartown to explore Chappaquiddick Island's vast nature preserves. It's a favorite place for bird-watchers and anglers.
West Tisbury. There's beautiful farm country out this way, and the 1859 Grange Hall is still the center of action. During the warmer months, don't miss the bountiful West Tisbury Farmers' Market.
Chilmark. The beaches here, best reached by bike, are spectacular. Quiet Chilmark is mostly residential, lacking any large downtown center.
Menemsha. An active fishing harbor, Menemsha is known for its splendid sunsets. There are a few shops and galleries, and a couple of excellent take-out spots for the freshest of seafood.
Aquinnah. Known until recently as Gay Head, Aquinnah is famous for its grand and dramatic red clay cliffs, as well as the resident lighthouse.