Add dates

Oak Bluffs Shore excursions

Our most recommended Oak Bluffs Shore excursions

From Boston: Martha's Vineyard with Optional Island Tour

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

Explore the beautiful island of Martha's Vineyard on a day trip from Boston. Visit the gingerbread cottages of Oak Bluffs, the town of Edgartown, the iconic lighthouse of Aquinnah, and more. Choose from either joining a fully guided tour or exploring the island at your leisure. Start your day with a 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. Admire the amazing gingerbread cottages in the town of Oak Bluffs, and see the town of Edgartown known for its whaling captains' homes and quaint downtown shops. Next, you will head to breathtaking Gay Head Cliffs and marvel at 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: 6 Town Island Group Tour

2. 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.

2 activities found
Sort by:

Other Sightseeing Options in Oak Bluffs

Want to discover all there is to do in Oak Bluffs? Click here for a full list.

What people are saying about Oak Bluffs

Wonderful experience! Jenny our shuttle driver was funny, knowledgeable, and nice! Tom was our guide through Martha’s Vineyard. He was so informative, providing wonderful history and interesting facts about the area. What a beautiful place! Thanks, so much!

Our driver Jennifer was fabulous! Funny, entertaining, & informative! She was the best. Tom, our guide on the 3 hour island tour was also amazing. He provided so much history & made the day so enjoyable! Highly recommend this excursion & a great value.

Long full day but very worth it - lots to see and great back stories. Tid bits about the Jaws movie filming locations and other history was valuable. Time to explore on your own at each stop. Great weather helped.

Definitely worth doing and taking the guided tour. Not sure how else you will be able to get around the island.

Excellent from start to finish. Incredible guide in Tom.