Discover the history of the Island's 6 unique towns! Your guides are passionate locals who will share their love of the island with you, so sit back and enjoy all this island has to offer!

First, you'll explore Oak Bluffs, a Victorian seaside resort that was built around the Methodist campgrounds. The campground is now known for its 300+ Victorian gingerbread cottages from the mid-1800s. Here, you'll also stop by the Flying Horse Carousel, one of the oldest platforms carousels still in use. You'll continue to Edgartown, a museum piece community with its historic harbor and waterfront, along with its white Greek Revival houses built by whaling captains carefully maintained to this day. You'll stop by The Old Whaling Church, the Edgartown Harbor Lighthouse and the historic Harborview Hotel.

You'll visit the busy harbor town of Vineyard Haven, the entry port to Martha’s Vineyard since the mid-1600s. You'll take a drive through the scenic up-island countryside passing through the historic farming towns of West Tisbury and Chilmark, making a 15-min stop in Menemsha an Idyllic fishing village where you can taste some clam 'chowdah' or 'lobstah bisque'. You’ll see the breathtaking multi-colored clay cliffs of Aquinnah and the impressive Gay Head lighthouse, where you'll have a chance to take pictures and stretch your legs.

On the drive back, you'll catch glimpses of centuries-old stone walls, views to the Atlantic shoreline, grazing livestock, rolling hills and historic homesteads. And the best part, you'll go over the bridge used in the filming of the movie Jaws!