First, you'll visit Oak Bluffs, a Victorian seaside resort known for its beautiful open-air tabernacle and the 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.
Then on 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.
Later you'll head on 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. You’ll see the breathtaking multi-colored clay cliffs of Aquinnah (Gay Head), with its impressive lighthouse where you'll have a chance to take pictures and stretch your legs.
On the way 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!