4 Essential Martha’s Vineyard Tours for Guided Island Sightseeing

The nuances of island history, architecture, and culture tend to hide in plain sight — if you really want to get to know them, guided Martha’s Vineyard tours are your best bet. Now, a number of Martha’s Vineyard tour companies will take your money, pack your group into a bus or van and try to show you the whole island in 2-3 hours. Here at Vineyard Square, we say slow down. Our favorite tours are either free, cheap, or offer a far greater value than your typical bus tour. Most of these Martha’s Vineyard tours are site-specific, so their guides have time for the details and you have time to explore before or after your tour.


Martha's Vineyard historic residence - Vincent House
Photo: Martha’s Vineyard Preservation Trust


Gingerbread Cottage Walking Tours – Oak Bluffs

The Martha’s Vineyard Camp Meeting Association gives walking tours of this historic community on Tuesdays and Thursdays in July and August, and private tours can be arranged. Known as the Campgrounds, the neighborhood — now clustered with pastel-colored Victorian cottages — began hosting religious meetings in 1835. The tours are inexpensive (free for kids!), and include admission to the Cottage Museum.


Edgartown Historic Property Tours

Step inside history with tours of Edgartown’s oldest properties. The Vincent House, Martha’s Vineyard’s oldest residence, was built in 1672 and is now a museum featuring rare colonial architecture and artifacts. Old Whaling Church, a popular Martha’s Vineyard wedding venue, includes original whale-oil lamps lit by prosperous captains in the 19th century. Dr. Daniel Fisher became one of the wealthiest men in the country during whaling’s heyday, and his elegant residence, too, is still standing. The Martha’s Vineyard Preservation Trust runs guided tours of all three of these properties on weekdays from Memorial Day to Labor Day. A bonus: they’re within easy walking distance of our Edgartown hotel.


African American Heritage Trail Tours

From Baptist gatherings in the 1800s to the Civil Rights movement to present day, African-American history runs deep on Martha’s Vineyard. The 27 stops along the African-American Heritage Trail span the entire island and include historic homes of notable residents, religious leaders, and political activists, along with meeting houses, cemeteries, and other points of interest. For a first-time visit, we recommend the 1.5-hour Oak Bluffs tour option, but if you’re feeling ambitious, the longer tours cover far more ground.


Mad Max Catamaran, Edgartown Harbor, Martha's VineyardMartha’s Vineyard Boat Tours

If you haven’t seen the island from the water, you haven’t really seen the island (no, the ferry doesn’t count!). This is the one Martha’s Vineyard tour option worthy of breaking our rules about pricing and sticking to one area. Consider the following three options, and be sure to book well in advance:
Mad Max Catamaran cruises daily out of Edgartown harbor, just a few blocks from Vineyard Square.
Magic Carpet is a wooden sailboat offering public tours and private charters and also departs from Edgartown Harbor. The Sunset Sail is one of our favorites.
Pirate Adventures is exactly what it sounds like and more—fun for the whole family on a custom-built pirate ship that sails around searching for treasure. It’s hands-down our favorite kid-friendly activity on Martha’s Vineyard.


Getting to Your Martha’s Vineyard Tour

Getting around the island (without bringing a car!) is easier than you might think. If you’re looking for a customized island tour and/or on-call transportation, Stagecoach Taxi is by far your best bet. Vineyard Transit Authority buses run frequently and reliably all summer. We’re always happy to assist our hotel guests with transportation needs at the Vineyard Square front desk.

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