See all six towns and uncover Martha's Vineyard stories
3 hours
Up to 14 people
Explore all six towns of Martha's Vineyard while learning about the island's history, architecture, and celebrity connections.
"What to expect Itinerary This is a typical itinerary for this product
Pass By: Joseph Sylvia State Beach, btwn Oak Bluffs and Edgartown off Beach Rd, Oak Bluffs, Martha's Vineyard, MA 02539
This state beach is famous for a scene which was filmed for the movie Jaws, and for the famous Jaws bridge where people jump off the bridge into the water all day.
Stop At: Aquinnah Cliffs, State Rd., Aquinnah, Martha's Vineyard, MA
Colorful clay cliffs located below the beautiful Aquinnah lighthouse
Duration: 15 minutes
Pass By: Aquinnah Lighthouse, Lighthouse Rd., Aquinnah, Martha's Vineyard, MA
A brick lighthouse, still operating, and positioned above the Aquinnah cliffs.
Pass By: Martha's Vineyard Camp meeting Association (MVCMA), 80 Trinity Park, Oak Bluffs, Martha's Vineyard, MA 02557
Gingerbread houses galore in this cute area which began as a religious gathering place in the 19th century.
Pass By: Flying Horses Carousel, 33 Lake Avenue, Oak Bluffs, Martha's Vineyard, MA 02557
This is the oldest platform merry-go-round in the country. If you grab the brass ring, you ride for free.
Stop At: Menemsha Public Beach, adjacent to Dutcher's Dock, Menemsha, Martha's Vineyard, MA
This is said to be the best beach for sunsets. It is also featured in the movie ""Jaws"" and is a great place for a quick chowder or lobster bisque.
Duration: 15 minutes
Pass By: Old Whaling Church, 89 Main St, Edgartown, Martha's Vineyard, MA 02539-8235
A majestic church built by whaling captains and is representative of the wealth they sustained during the whaling industry period.
Pass By: Edgartown Lighthouse, 121 N Water St, Edgartown, Martha's Vineyard, MA 02539-8016
A stately lighthouse built in the early 1800's, overlooking Edgartown harbor and Chappaquiddick. "
Free cancellation up to 24 hours before start. No refund for cancellations within 24 hours, and changes within 24 hours aren't accepted. If canceled due to poor weather or too few travelers, you'll be offered a different date or experience, or a full refund.
The full-island tour can accommodate up to 14 people.
1 Seaview Ave, Oak Bluffs, MA 02557
The majority of travelers rave about their guides here, with Harry, Liz, and Michelle earning particularly enthusiastic praise for their deep local knowledge and engaging storytelling. These guides clearly know the island inside and out, sharing historical insights and cultural perspectives that bring Martha's Vineyard to life during the three-hour tours. The owners also get kudos for being accommodating and going above and beyond when unexpected situations arise. That said, experiences can vary significantly depending on which guide you get. A few visitors report inconsistent tour content, with some guides focusing more on personal restaurant recommendations than historical information. There have been isolated complaints about miscommunication regarding itinerary details and tour start times. The vans can feel cramped with larger groups, which might limit photo opportunities at stops. When you book, consider asking specifically for one of the highly-rated guides if possible, as the quality seems tied directly to who's behind the wheel.
Well done! Anthony was detailed & entertaining. Bus was good & comfortable. The Aquinnah tour is a good one. Aquinnah is very cool. Even met the owner while checking in before our trip.
Dave Robach
June 26, 2026
Well done! Anthony was detailed & entertaining. Bus was good & comfortable. The Aquinnah tour is a good one. Aquinnah is very cool. Even met the owner while checking in before our trip.
Dave Robach
June 26, 2026
Pick up a bike in Oak Bluffs and ride the island your way
Get a 7-day bike rental delivered to your address in Oak Bluffs
Pick up a weekly bike rental and explore Martha’s Vineyard your way
Explore by bike with delivery, helmets, locks, and baskets
Pick up your bike steps from the ferry and ride Martha’s Vineyard for 1–6 days