A Comparison of Martha’s Vineyard Tours

by Mélissa Lesnie  |  Published September 6, 2022

Pristine beaches, rugged cliffs, quaint cottages… Explore the historic Massachusetts island of Martha’s Vineyard on a guided tour with a local: the best way to experience a slice of island life. 

Gingerbread house cottages, Martha’s Vineyard (photo: Viator)

Treasured summer vacation spot of the Kennedys, Clintons and Obamas, Martha’s Vineyard is the American Dream condensed onto a 100 square mile island. The mom-and-pop stores are alive and well, picket fences are plentiful, and the pace of life is leisurely. New England’s largest island just off Cape Cod has lost none of its old-world charm and natural beauty. The peace hasn’t been disturbed here since the 1970s, when the small fishing village of Menemsha was taken over by a certain mechanical shark for the set of Steven Spielberg’s Jaws.

A guided tour allows visitors to sample the island’s diverse delights, from the Victorian architecture of its distinctive ‘gingerbread’ cottages to the untamed coastal cliffs, all while offering insight into the area’s unique history. Long before the crisp green lawns and sparkling harbor views came the Methodist Campgrounds, a significant deaf community and and the island’s own sign language, a settlement of freed and escaped African American slaves, the wealth of the 19th-century whaling industry, and the deep-rooted ancestral heritage of the Wampanoag people. Whether enjoying a daytrip from the mainland or to get your bearings for a longer stay, here are three ways to see all Martha’s Vineyard has to offer.

Martha’s Vineyard 6-town Island Group Tour

This three-hour cirtcuit departs from the idyllic town of Oak Bluffs, where you can admire some 300 Carpenter Gothic ‘gingerbread’ cottages in the colorful style that is just so eye-catchingly Martha. The colors are no less bold on the oldest carousel in America, operating here since 1876. Other stops on this comprehensive tour of six historical towns include the seaside village of Edgartown, with its white, Greek revival architecture (home to the famous Jaws bridge). Groups are limited to 14 people to ensure a personnalized experience. The tour includes a complimentary map and two 15-minute breaks to explore the charming fishing village of Menemsha (lobster bisque, anyone?), and the rugged clay Aquinnah Cliffs boasting a panoramic view from the island’s most western point. Ideal for a first-time visit to Martha’s Vineyard. From $55/person

Reserve via

All-Island Tour of Martha’s Vineyard

Lighthouse and cliffs, Martha’s Vineyard (photo: Homegrown Tours)

Plenty of photo opportunities on this three-hour bus or minivan tour of Martha’s Vineyard, in the company of 3rd and 7th-generation Vineyarders.  From the meeting point of Oak Bluffs (you’ll see why it was one known as ‘Cottage City’), you will explore the island’s oldest port at Tisbury, before heading from the western side to the south shore to see the stunning chain of Elizabeth Islands. The bus is fitted with a screen that displays 19th-century photographs of the sites visited to help you understand how much (or how little) Martha’s Vineyard has changed. Film buffs will not be disappointed, with several stops revealing where scenes from Jaws were filmed. A gift bag including maps, coupons from local business and handmade trinkets will see you on your way. From $55/person

Reserve via

Martha’s Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

Explore Martha’s Vineyard from Boston (photo: Viator)

Getting onto the island can be daunting for first-time visitors. Relax and make the journey an enjoyable part of your day trip to Martha’s Vineyard with this scenic round-trip tour from Boston. With hotel pickup or departure direct from the Boston Marriott Long Wharf, an air-conditioned mini coach bus will whisk you away to Cape Cod. From there, step aboard the Island Queen for a 40-minute ferry cruise to Martha’s Vineyard, complete with panoramic ocean views and salty air. You will have up to six hours to explore the island at your own pace, with the option of upgrading to a 3-hour narrated island tour stopping in Edgartown, Vineyard Haven, downtown Falmouth or Gay Head Cliffs, among other locations depending on the season. From $110/person

Reserve with