About 30 miles east of Block Island, Martha’s Vineyard sits 10 or so miles south of Cape Cod. While the island is only home to around 15,000 year round residents, its close proximity to Boston and its easy ferry access from the cape means that the summer population swells to 200,000 people.

Madrone on her way to Martha’s Vineyard. Photo courtesy of S/V Helios

Originally home to the Wampanoag tribe, many of the European settlers of Martha’s Vineyard became wealthy during the peak of the whaling industry in the early- to mid-1800s. Some of that wealth is still evident today in the lines of perfectly preserved seaside mansions once owned by the whaling captains and ship owners.

One of the many Edgartown Harbor homes

The eastern edge of Martha’s Vineyard features the town of Edgartown and its eponymous harbor, situated between the main island and the small outer island of Chappaquiddick. Because of the popularity of Edgartown Harbor, anchoring is not allowed – instead the town has installed permanent mooring buoys both to better protect the bottom of the harbor against dragging anchors and chain and to allow more boats to fit in the harbor.

Cedar shingles and crisp white trim- a common site in Edgartown

If Disney made an attempt to recreate the iconic New England seaside village, Edgartown is what it would look like. Everything in sight is covered in either weathered cedar shakes or pristine white paint, and every building in town looks like it was built in the 1800s. A small 2-3 car ferry creeps across the harbor to Chappaquiddick, watched over by the Edgartown Lighthouse. Graceful summer homes dot the sides of the harbor, fronted by perfectly manicured lawns, docks, and boathouses.

A guest cottage with a lovely dahlia garden in quaint Edgartown

With a strong maritime heritage around her, Madrone felt right at home tied to her buoy in the Edgartown Harbor. Without pressed trousers, neat collared shirts, and yacht club hats, however, her salty dirtbag crew felt a little bit out of place…

A visit to the town lighthouse
Lovely sunset at our mooring