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Oak Bluffs Tours

Our most recommended Oak Bluffs Tours

Martha's Vineyard: 6 Town Island Group Tour

1. Martha's Vineyard: 6 Town Island Group Tour

Tour the 100 square mile island of Martha's Vineyard and hear the charming history of its 6 towns from a local guide. As you drive across the picturesque island, admire curiosities like America's oldest carousel and the cliffs of Aquinnah. Start in Oak Bluffs, known for its distinctive Victorian architecture with 300 colorful cottages designed to look like gingerbread houses. Turn a corner and see "The Flying Horse Carousel," America’s oldest carousel, operating since 1876. Continue to Edgartown, with its quaint harbor complete with an 80-year-old lighthouse. A former hub for the whaling industry, admire the stately Greek revival mansions built by ship captains. Travel along the idyllic countryside and small fishing villages before stopping for some clam chowder or lobster bisque in Menemsha. Next, arrive at the technicolor cliffs of Aquinnah before swinging by the bridge made famous in the movie Jaws.

Martha's Vineyard: All Island Tour

2. Martha's Vineyard: All Island Tour

Sit right back and enjoy the most unique tour on Martha's Vineyard. Hop on an exciting fun-filled bus and hear about the fascinating history of the area narrated by 3rd and 7th-generation islanders.  Start at the amazing town of Oak Bluffs (once known as Cottage City) where you will learn about the Methodist Campgrounds and their history of bringing tourism to MV.  Next, travel through Vineyard Haven (also known as Tisbury), the oldest port of 200 years, and hear about the hardships of living on an island devastated by fire in 1888 and ransacked by General Grey in 1778.  See the beautiful vistas of rolling hills and ancient stone walls as you make your way to the western side. Learn about the af/am heritage and how the island became a stop on the underground railroad.  Hear about the indigenous peoples of Martha's Vineyard and how Thomas Mayhew converted the Native Americans to Christianity. After this, the south shore and two sounds blanket the island and have a gorgeous chain of islands called the Elizabeth Islands that have an amazing history of their own. Watch a screen that shows what certain sites looked like in the 1800s to get a better view of how the area has evolved.  Don't forget the movie JAWS, there will be many sites to see where all the scenes from the movie were filmed. End the tour with a gift bag including maps, guides, coupons, and handmade trinkets. There are plenty of opportunities for photos and much more.

Other Sightseeing Options in Oak Bluffs

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What people are saying about Oak Bluffs

Our guide was the best! (I can’t remember his name? He uses his first name and the first letter of his last long Italian name.). He was informative and very knowledgeable of the area. He also had a sense of humor. Loved the different towns!

We had areally great tour with an excellent driver/guide in a small bus. Really well done.We saw a lot of tje island and learned a lot about it! First class.

Very enjoyable tour with much information about MV. We had a full van that was a little snug until a party of 5 left the tour early.

Awesome Guide; interesting material and sites covered and comfortable accommodations!

Our guide did a great job!! He was so knowledgeable!