Historic Tours of Martha’s Vineyard

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


Daily History



Sunset Trips

to Menemsha 



Private Tours



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


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 13 seats per tour, you’ll feel like you are on your own private tour of the island.

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.

Boarding Locations

How to Purchase Tickets
Tickets are $45 and can be purchased online, via phone 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. Call: 508-684-8595


Take a Sunset Trip to Menemsha

Let us take you to one of the best spots to watch the sunset on Martha’s Vineyard! Enjoy a trip to the Menemsha beach in one of our luxury vans. We’ll provide a cooler well-stocked with refreshments for the ride and help place an order at one of the famous Menemsha seafood spots. Once you arrive, you can to pick up your order and head to the beach for the beautiful sunset.

Details: Van departs from the Dockside Inn one hour before sunset, and will pick up at the beach for the return trip one hour after sunset. Trip from the Dockside to Menemsha is approximately 30 minutes.

Book your trip: Give us a call at 508.684.8595 (tours are weather dependent)

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