Trolley Tour Fast Facts:

  • 2.5 hour tour, including a one hour stop in downtown Edgartown
  • Visit 4 Island towns: Oak Bluffs, Vineyard Haven, Edgartown & West Tisbury
  • $33/pp
  • Accommodates up to 28 passengers
  • Available for private groups and charters
  • No reservations required

Our air conditioned vintage trolleys are a great way to explore Martha's Vineyard in style, with a capacity of up to 15 passengers. MV Sightseeing offers the only trolleys available on Martha's Vineyard. Step aboard and step back in time, and see what makes Martha’s Vineyard one of the most beloved summer destinations.

 A MV Sightseeing trolley tour is the perfect introduction to Martha’s Vineyard, while enjoying a leisurely, comfortable ride. Learn local history and insider information from our knowledgeable bus drivers, while visiting four of the Island's most popular towns, and including a one hour stop in the historic village of Edgartown, known for it's whaling history and quaint architecture. 


On the tour we'll explore:



The lively, diverse town of Oak Bluffs was originally incorporated under the name of Cottage City in 1880. The town served as a popular Methodist revival campground in the 19th century, which gave way to the brightly colored, "gingerbread houses” that decorate the town today. Idyllic Ocean Park is home to a waterfront gazebo and iconic victorian estates, as well as the Island’s annual kite festival and spectacular July 4th firework display. Nearby we'll pass the bustling Oak Bluffs Harbor; Flying Horses Carousel, the nation’s largest operating carousel; and Circuit Ave., the town’s busy main drag.



Neighboring Vineyard Haven is a quieter town, where we find the year round Steamship Authority terminal and the original Black Dog Tavern and Wharf, as well as the world renowned Shenandoah and Alabama tall ship sail boats. “VH” as the locals call it, offers a quaint Main Street with boutique shops, art galleries, cafes and restaurants. Vineyard Haven is also home to the historic Capawock Theater and future home of the Martha’s Vineyard Museum.



Our tour also includes a town “up-Island,” how the locals refer to the west side of Martha’s Vineyard. We'll pass through the town of West Tisbury, a quaint, rural town that’s home to the famous summer farmers market, and a bustling artisans festival that showcase the work of local artists and makers. You'll also get a glimpse of the Agricultural Hall, a reconstructed century-old post-and-beam barn brought to the Island from New Hampshire, which hosts the popular Ag Fair.



The tour also includes a one hour stop in Edgartown, a picturesque resort community that once served as one of the the world's most popular ports during the whaling boom of the 1800s. Historic clapboard Captain’s homes line the downtown, paying homage to the town's past, along with the iconic Edgartown lighthouse.


Our one hour stop allows you to get out and explore the various shops, art galleries, and world class restaurants that line the downtown streets. Grab a bite to eat, and a souvenir, walk along the Edgartown harbor, or visit historic landmarks including the Old Whaling Church and Daniel Fisher House.


Our Trolley Tour will leave you chock full of Island history and knowledge, and serves as a great introduction to the four most popular towns on Martha's Vineyard. 

Learn more about the history of trolleys on Martha's Vineyard here