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 and famous whaling ships and captains, to its pristine beaches and geological marvels, there is a story behind it all. Our local tour guides  know the history behind all the beauty.

*Our regular season has ended and we are available on a limited basis. Please call 508.684.8595, for availability.

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 sightseeing 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 Horses Carousel
East Chop Lighthouse

West Tisbury
Alley’s General Store
Grange Hall
Field Gallery

Gay Head Light House
Clay Cliffs
Aquinnah Cultural Center

Historic Sea Captains’ Homes
Edgartown Lighthouse

Stone Walls of Chilmark
Beetlebung Corner
Seven Gates Farm

Vineyard Haven
Martha’s Vineyard Museum
Tashmoo Overlook
Tisbury Harbor


Your Martha’s Vineyard sightseeing tour begins as we travel from Oak Bluffs to Vineyard Haven along Vineyard Sound and the Vineyard Haven harbor front. Your knowledgeable tour guide will keep you entertained and interested with insider Vineyard knowledge. 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 where you will have time to explore the Gay Head Lighthouse, see the famous clay cliffs, visit the cliff side shops or grab a bowl of the Island’s best clam chowder at Cliffhangers!

Your Martha’s Vineyard tour concludes in Oak Bluffs at the Cottage Museum in the “Campgrounds,” also known as the Martha’s Vineyard Camp Meeting Association (MVCMA). With its more than 400 Gingerbread Cottages and historic Tabernacle, the Campgrounds are a must-see for every visitor to Oak Bluffs. 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 in the Campgrounds in the 1800s. Also on display are vintage photographs and other interesting documents relating to the history of the Campgrounds.

Once you’ve had a leisurely stroll through the Campgrounds, you can visit the many shops and restaurants of nearby downtown Oak Bluffs.

More Tour Info

Martha’s Vineyard 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.

*Our regular season has ended and we are available on a limited basis. Please call 508.684.8595, for availability.

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 knowledge! We worked with the Martha’s Vineyard Museum to craft a compelling tour narrative that weaves contemporary and historic events together as you explore the island. 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. Your Martha’s Vineyard sightseeing tour includes admission to the Campground Cottage Museum.

Martha’s Vineyard Camp Meeting Association

Visit the Museum’s website