Martha's Vineyard: 3-Hr Island Charm Tour from Oak Bluffs
Experience our famous 3-hour full Island tour for a budget friendly rate! Our tour drivers - native Islanders & long-time "wash-a-shores" have years of tour driving experience and the best reviews to show it! This 3-hour tour will introduce you to our 100 square mile island by giving you the history, both past and present, of our 6 unique towns. In all, 2 ½ hours of the tour is narrated, and you'll have a stop at the beautiful Cliffs of Aquinnah. Top highlights on this tour include Oak Bluffs, Edgartown, Vineyard Haven, Aquinnah, West Tisbury, Chilmark, and Menemsha. So join us in our comfortable air-conditioned vans & get ready to make memories for a lifetime - your Martha's Vineyard tour! (Children under 10 excluded from this tour.)
Reviews
Reviews and Rating (Tripadvisor)
5 stars
Reviews by Tripadvisor travelers
Dmarkwind, 11/19/2025 5:29:01 PM
Our guide, Phil, started our tour off a little shaky with some bad dad jokes, but quickly showed himself to be a skilled and knowledgeable tour guide. Phil said he grew up in Martha’s Vineyard, but can’t afford to live on the island year-round. He sure knew his way around and the history of a lot of different things on the island. He told us that as a 10-year old, he was an extra in the “out of the water” scene in Jaws, and shared a lot of other great stories about the island, including about times he was a bartender to Bill Murray, and some of his encounters with other famous people. Our tour vehicle was 15-person private van, but Phil said he preferred his tours stay in the 10-12 range, which ours was. Those other tours with busses would have never been able to pull off the road in some of the tight spots Phils stopped at to point out some interesting sites and details. We visited all the cities on the island and saw centuries-old stone walls, great views of the Atlantic, rolling hills & the bridge used in Jaws. There was only one stop where we actually got out and left the van, and that was at Gay Head cliffs and lighthouse, where we had about 20 minutes to take a short walk to a high point on the island. This has nothing to do with Phil, but I wish the ticket we purchased for this tour through Groupon had the Martha’s Vineyard Tours and Transportation name on it, because we didn’t know which of the literally dozens of tour operations we were looking for, but it worked out. We learned that there were definitely cheaper tours we could have taken, but for our first Martha’s Vineyard experience, we were happy with this one, and would highly recommend Phil and this tour!
Navigate68337241757, 11/1/2025 1:06:16 PM
Our tour guide was outstanding. Informative and personality plus. He covered the amazing history of MV with a personal touch that made this trip amazing.
robert r, 10/16/2025 10:06:35 AM
The tour guide was very knowledgeable and friendly. We learned a lot about the island history and seen some great sights
890dickw, 10/15/2025 4:11:10 PM
My wife and I throughly enjoyed this 3 hour tour and the wealth of information that Bart shared through this van tour around the island. Bart shared local community information, natural environment information, historical information, insights about important cultural events and celebrities who are involved with Martha's Vineward. Well done. Only wish would have been more time to take photos or get out to explore.
awimberg, 10/14/2025 11:06:57 AM
Loved this tour and the tour guide was VERY knowledgeable and interesting. He had a lot to add from a personal perspective having lived on the island for 50 years. The van was very comfortable and cool. I only wish there were more brief stops and a longer stop at Aquinnah. Totally worth the price.
Hanspeter P, 10/12/2025 1:24:29 PM
Ken was an excellent and knowledgeable tour guide. The van was comfortable and the tour was very informative. We had a great experience and highly recommend it.
hangtenmike, 10/11/2025 7:51:10 PM
Fabulous tour with Phil! Phil generously shared both his first hand knowledge of regional history and current events with many compelling stories. Phil is relatable, likable, knowledgeable, articulate, and fun. We highly recommend this tour and Phil.
Kris_B, 10/11/2025 10:24:42 AM
I really enjoyed this tour. Guide was very knowledgeable about the area because he grew up here. Loved learning about the history and hearing all the stories of the island! Highly recommend the tour!
Deborah_C, 10/10/2025 9:25:28 AM
Interesting to see and hear about the homes and how they came to be built. The Gingerbread Cottages were fun!
Marilyn_H, 10/8/2025 2:24:35 PM
Tour guide was very informative and funny rainy day but guide still was trying to make it a fun trip
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- CANCEL 24 HR IN ADVANCE
- Operates in all weather conditions, please dress appropriately
- Minimum age for children is 10 years
- Tours depart Diagonally across the street from the Oak Bluffs Steamship Authority Ticket Office. Near Soldier Statue. Look for mini-bus or van marked "MV Transport" along the curb in front of the ticket office.
- During Check out Please use Special Requirements and let us know what Ferry you will be taking to the island. Thank you
- No refunds or rescheduling of reservations unless 24 hours prior to tour date & time.
- If you area taking the Hyline Fast Ferry from Hyannis, The New Bedford Seastreak, or the Rhode Island Fast Ferry (Quonset Point) Please make those reservation first to assure you getting to the island on time before booking with us
- You MUST BE ON the island of MARTHA'S VINEYARD to do this tour
- Children must be accompanied by an adult
- No Children under the age of 10
Departure point
At the Soldier Statue Diagonally Across the Street On The Island of Martha's Vineyard MUST BE ON MARTHA'S VINEYARD Please let us know in special requests what ferry you are taking to get to the island. This information is important incase your ferry gets diverted to another location portReturn details
Experience our famous 3-hour full Island tour for a budget friendly rate! Our tour drivers - native Islanders & long-time "wash-a-shores" have years of tour driving experience and the best reviews to show it! This 3-hour tour will introduce you to our 100 square mile island by giving you the history, both past and present, of our 6 unique towns. In all, 2 ½ hours of the tour is narrated, and you'll have a stop at the beautiful Cliffs of Aquinnah. Top highlights on this tour include Oak Bluffs, Edgartown, Vineyard Haven, Aquinnah, West Tisbury, Chilmark, and Menemsha. So join us in our comfortable air-conditioned vans & get ready to make memories for a lifetime - your Martha's Vineyard tour! (Children under 10 excluded from this tour.)Redemption
Meeting Location: Tour Depart from the Memorial Soldier Statue Located diagonally across the street from the Oak Bluffs Steamship Authority Ticket Office (1 Seaview Ave) You will look for van/van's marked with "MV Transport". If you can not find us Please Call 508-939-1359. Thank you Please see directions from ferries under departure point. Times are subject to change due to local traffic conditions. Due to the nature of this tour and the safety of all guests, the tour operator reserves the right to refuse service to passengers who are intoxicated or show signs of intoxication. If, as a result, your tour is canceled, you will not be entitled to a refund.24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund






