Seven miles off the Cape's southern shore, Martha's Vineyard sits close enough for a day trip but feels far enough to be a genuine destination. The ferry from Woods Hole takes 45 minutes, and by the time the island's waterfront comes into view, you're already somewhere different.
Morning: Catch the Early Ferry and Start in Oak Bluffs
The Steamship Authority runs year-round car and passenger ferries from Woods Hole to Vineyard Haven. For a day trip, take the passenger ferry. Check the Steamship Authority's schedule and book your ticket in advance.
You'll dock in Vineyard Haven, but Oak Bluffs is your first stop. It's a short bus or cab ride east. The Martha's Vineyard Camp Meeting Association neighborhood — a grid of tiny, candy-colored gingerbread cottages built starting in the 1830s — is one of the most genuinely unusual streetscapes in New England. Walk the lanes around Trinity Park and the iron-and-wood Tabernacle at the center. Then find the Flying Horses Carousel on Circuit Avenue — the oldest continuously operating platform carousel in the United States, built in 1876.
Midday: Edgartown and State Beach
Edgartown is a 20-minute bus ride south of Oak Bluffs along Beach Road, which runs beside the island's famous State Beach on Nantucket Sound — calm water, warm-ish temperatures. Edgartown itself is compact, colonial, and expensive in a very deliberate way. The white-clapboard captains' houses along North Water Street were built by 19th-century whaling money. Walk down to the Edgartown Lighthouse at the harbor's edge.
Afternoon: Up-Island to Aquinnah
The island's character changes completely once you leave Edgartown and head up-island. West Tisbury and Chilmark are agricultural — stone walls, horse farms, working fields, and farm stands.
Menemsha, Chilmark's fishing village, sits on Vineyard Sound with a working harbor and a cluster of fish shacks. Continue west to Aquinnah. The Aquinnah Cliffs — multi-colored clay cliffs rising 150 feet above a lighthouse and a beach — are at the island's western tip, on land owned and managed by the Wampanoag Tribe of Gay Head (Aquinnah).
Evening: Sunset Over Vineyard Sound
Menemsha is the place to be at sunset on Martha's Vineyard. The village faces west over Vineyard Sound, and the sunsets here are legitimately famous. Then catch a later ferry back to Woods Hole.
Practical Notes
Getting there: The Steamship Authority runs year-round passenger and car ferries from Woods Hole to Vineyard Haven. The crossing takes 45 minutes. Book passenger tickets in advance in summer.
Cars: Leave the car on the Cape for a day trip. Bus service between Vineyard Haven, Oak Bluffs, and Edgartown is reliable in season.
Timing: An early ferry departure (7am or 8am from Woods Hole) gives you enough time to do both the down-island towns and the up-island run.
