Historic Tours of Martha’s Vineyard

Tour the island in our new, super comfortable air conditioned luxury vans.

Martha’s Vineyard is a small island with a big history. From its timeless architecture, famous whaling ships and captains, to its pristine beaches and geological marvels, there is a story behind it all. Our local tour guides, in conjunction with the Martha’s Vineyard Museum, know the history behind all the beauty.




Our luxury vans are available for Weddings, Special Events & Private Rentals.


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Tour Information

Join us for a 2.5 hour narrated tour of all six towns, including a mid-tour stop at the beautiful Aquinnah.

Each tour offers a full interactive narrative on Martha’s Vineyard’s rich history—written in conjunction with the Martha’s Vineyard Museum’s historical curator. With only 14 seats per tour, you’ll feel like you are on your own private tour of the island.

Oak Bluffs
Gingerbread Cottages
Flying Horse Carousel
East Chop Lighthouse

West Tisbury
Alley’s General Store
Grange Hall
Field Gallery

Gay Head Light House
Clay Cliffs
Aquinnah Cultural Center

Martha’s Vineyard Museum
Historic Sea Captains’ Homes
Edgartown Lighthouse

Stone Walls of Chilmark
Beetlebung Corner
Seven Gates Farm

Vineyard Haven
Mariners’ Hospital
Tashmoo Overlook
Tisbury Harbor

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Your tour begins as we travel from Oak Bluffs towards Vineyard Haven, along the beautiful ocean coast. Your knowledgeable tour guide will keep you entertained and interested with insider Vineyard knowledge enhanced by a collection of historic photos to see how the Island has changed over the years. As you continue, you will see beautiful and enchanting island vistas, historic sea captains’ homes, scenes from Jaws, and much more. There is a 30 minute comfort stop in Aquinnah were you will have time to explore the Aquinnah Lighthouse, see the famous clay cliffs, visit local shops or grab a bowl of the Island’s best clam chowder.

Your tour concludes at the Martha’s Vineyard Camp Meeting Association’s Cottage Museum in Oak Bluffs, located right in the heart of the Campground, with its more than 400 Gingerbread Cottages and historic Tabernacle. Entry to the MVCMA Cottage Museum is included with your tour van admission and you can view the interior of a typical Campground cottage, complete with period furnishings offering a glimpse of life on the Campgrounds in the 1800s. Also on display are vintage photographs and other interesting documents relating to the history of the Campground.

Once you’ve had a leisurely stroll through the Campgrounds, you can head a few steps away to the many shops and restaurants of Oak Bluffs.

More Tour Info

Tour Times
We have four vans, and tours leave twice a day at approximately 10:30 am and 2 pm, from the Dockside Inn in Oak Bluffs. Departure times may vary slightly due to the ferry schedule so be sure to check with us for the daily schedule.

Boarding Locations

How to Purchase Tickets
Tickets are $45 and can be purchased online or daily, between 7 am and 3 pm in the lobby of the Dockside Inn. If seats are available, tickets can be purchased on the spot from the van drivers. Cash or charge.


Our Vineyard Partners

What makes our tours unique? Our fantastic Vineyard partners! In collaboration with the Martha’s Vineyard Museum, we worked to craft a compelling tour narrative that weaves contemporary and historic events as you explore the island. Additionally, the MV Museum graciously shared photos from their archive with us, and you’ll be able to see the them on your tour and compare the Island “then and now.” Our partnership with the Martha’s Vineyard Camp Meeting Association allows us to make our final stop in the heart of the Gingerbread Cottages in Oak Bluffs, and your tour includes admission to the Campground Cottage Museum.

Martha’s Vineyard Museum

Visit the Museum’s website

Martha’s Vineyard Camp Meeting Association

Visit the Museum’s website