On our tours, you will experience six diverse towns and explore unique places. By the end of our journey, we will have traveled 60 miles, and it goes by fast.
Touring this special place is made even better with convenient pick-up service wherever you stay in our comfortable and air-conditioned vans.
In Oak Bluffs, we’ll walk among the story-book gingerbread cottages and see the oldest carousel in America. Here, if you grab the brass ring, you get a free ride! We’ll stroll along the lively little harbor or meander through Ocean Park.
Vineyard Haven is a quaint New England shopping village where you can go for a sunset sail on a large schooner. Wander up and down Main Street, which is filled with cute shops and restaurants.
West Tisbury is home to the oldest store on-island, Alley’s General Store, which first opened in 1858. We’ll visit the art at the Field Gallery across the road and perhaps pose with the whimsical nude statues.
Edgartown is surreal, with a harbor and waterfront edged by stately white Greek Revival houses built by whaling captains. The Old Whaling Church stands tall thanks to six massive columns, and along with the Edgartown Harbor Lighthouse and the historic Harborview Hotel, Edgartown really belongs in a museum!
Onwards to Menemsha, we drive past rolling hills that run to the sea, dotted with sheep and horses and framed by the miles of British-style stone walls. A stop at Menemsha fishing village is a must!
In Aquinnah, the end of the island, witness our magnificent colorful clay cliffs. Look down on the spectacular beaches and scour the horizon for the Elizabeth Islands off in the distance. Visit the unique shops owned by the Wampanoag tribe to purchase a piece of wampum jewelry. If you’re feeling energetic, climb to the top of the Gayhead lighthouse, which we moved a couple of years ago so it wouldn’t fall into the sea!
We will pick you up in our air-conditioned vans from your ferry dock, hotel, or rental home and begin your tour. We have a morning, afternoon, and sunset tour.