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Things to do in

Oak Bluffs

Our most recommended things to do in Oak Bluffs

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.

From Boston: Martha's Vineyard with Optional Island Tour

2. From Boston: Martha's Vineyard with Optional Island Tour

Start your day with pickup from your downtown Boston hotel in a mini-coach for the 1.5-hour journey to the ferry in Falmouth, Cape Cod. Enjoy complimentary snacks and bottled water while browsing the Martha’s Vineyard guidebook as you plan your 6 hours on the island. After a short ferry ride, prepare to discover the beautiful island. Choose from either joining a 3-hour guided tour or exploring it at your leisure. For both options, you will be provided with a discount card valid at some of the island's restaurants and attractions. Be sure to visit the amazing gingerbread cottages in the town of Oak Bluffs. See the town of Edgartown known for its whaling captains' homes and quaint downtown shops. Head to breathtaking Gay Head Cliffs and see the famous lighthouse in the town of Aquinnah. Bike and jeep rentals are available for purchase or use public transportation to see the island. After your day on Martha's Vineyard is complete and you return on the ferry, sit back and relax on your comfortable minibus ride back to Boston.

Martha's Vineyard: All Island Tour

3. 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.

Martha's Vineyard: Self-Guided Audio Driving Tour

4. Martha's Vineyard: Self-Guided Audio Driving Tour

Experience the highlights of one of Massachusett's most beloved islands and popular vacation spots. Take advantage of the flexibility to set your own pace between stops during the self-guided app-based audio tour. Start by downloading the Action Tour Guide app that will function as your personal guide, audio tour, and map all in one. Begin your tour of Martha’s Vineyard right off the ferry in Vineyard Haven. As you drive along the coast, you’ll hear about the Wampanoag tribe and how the island got its unusual name. See the characteristic architecture of past times starting with the 1876 Flying Horses Carousel. Admire the delightful pastel facades of the "gingerbread houses" in Oak Bluffs and the community's treasured Tabernacle campground. Visit a neighborhood museum to enrich your visit and find a souvenir. Next, you’ll head to Inkwell Beach, a beautiful stretch of sand with an unfortunate history. Find out how a genetic mutation resulted in Martha’s Vineyard residents creating their very own form of sign language. As you continue south, you’ll learn more about how the island fared during the tumultuous times of the American Revolution. Afterward, see the beach where Steven Spielberg filmed an iconic scene from the movie Jaws. Feel a connection with the natural world as you discover the flora and fauna of Caroline Tuthill Wildlife Preserve. Next, you’ll reach Lighthouse Beach, home to an iconic lighthouse that was originally built almost 200 years ago. Step back in time as you pass through the quaint historic district of Edgartown. Hear about the island’s mysterious disappearing deer and the 1938 New England Hurricane, which devastated local communities. Your tour will end in South Beach, where you will discover a placid bay and dramatic beach in the same setting. The audio tour is curated by local guides and creative writers and is narrated by professional voice artists. Most stops along the tour have animated videos allowing you to visualize what you cannot see, such as snapshots from different centuries or building interiors.

Other Sightseeing Options in Oak Bluffs

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What people are saying about Oak Bluffs

Overall rating

4.5 / 5

based on 370 reviews

I had a wonderful experience! As a first timer, having the 3 hour narrated tour was a great introduction to the island and learning about its history. It gives a great set up to be able to roam the island on your own for the next time. I highly suggest this tour!

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!

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.

The trip was well organized. We rented E-bikes and spent the day exploring the island.

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