Most visitors take the ferry service connecting the Vineyard and the mainland. If you’re driving from Boston it’s around a 90-minute trip to Woods Hole, Massachusetts, from where the state-run Steamship Authority ferries are the only option to accommodate cars, making multiple trips a day to Martha’s Vineyard. If you choose to bring your car aboard, a reservation will be needed to secure a spot but walk-ons are always welcome. Ferries dock in Vineyard Haven year round, and in Oak Bluffs mid-May through mid-October. There is also a seasonal passenger ferry service, including Island Queen from Falmouth, Hy-line Cruises from Hyannis, and Martha’s Vineyard Fast Ferry from North Kingston, Rhode Island.
Stay: The Mansion House Inn is ideal for couples or families. It’s the only Island inn to offer an indoor pool and modern fitness centre with regular classes, and is located just two blocks from the year-round ferry terminal. In the heart of the newly established Vineyard Haven Harbor Cultural District, you’re in the middle of it all. For a distinctive inn experience with lovely water views and smashing breakfasts, check into The Crocker House Inn.
Eat: For dinner, it’s the Copper Wok, a newly opened hotspot that is already touted as a favourite among Islanders and visitors alike. You’ll delight in their saki-based cocktails and Asian-fusion. And no Vineyard trip is complete without a traditional visit to The Black Dog Tavern, a famous low-key family-friendly pub. For breakfast, try Art Cliff Diner or Nat’s Nook, the Island’s only creperie.
To Do: Explore the Vineyard Haven Harbor Cultural District for shopping and gallery hopping. Stop at Bunch of Grapes Bookstore for fact or fiction, and then visit Nat’s Nook’s some coffee and quiet reading time. Once you’re done, head up to the cupola of Mansion House for an incredible unobstructed view of the harbour. Get ready for the trek to the West Chop Lighthouse.
Stay: A charming small inn that overlooks the ocean, Isabelle’s Beach House has a huge front porch that you’ll never want to leave.