A favorite summer resort for more than a century, New England's largest island attracts the rich and famous, from movie stars and presidents who arrive by private plane, as well as legions of day-trippers disembarking from the ferry. Chances are they will all find what they're looking for.
Want a postcard-perfect whaling village with immaculate 19th-century homes? Go to Edgartown. Gentle hills leading to the sea? Try Chilmark. Woods and pastoral farms complete with stone walls? Head for West Tisbury. A day at the beach? Plenty to choose from (and if you're renting a house, you'll likely have access to a fine private community strand). Shopping break? Stroll through Vineyard Haven, where galleries and boutique shops cater to most of the island's year-round residents.
The best way to explore is to pedal the roads and paths, such as the scenic 6-mile seaside stretch between Edgartown and Oak Bluffs. In the end, what will you remember? Perhaps a flawless summer day, beach dunes, and a lobster picnic far from the rest of the world.