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Things to do in
Oak Bluffs

Our most recommended things to do in Oak Bluffs

Boston: Discover Martha's Vineyard with Optional Island Tour

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

Fall in love with the scenic island of Martha's Vineyard on a day trip from Boston. Admire the gingerbread cottages of Oak Bluffs and the iconic lighthouse of Aquinnah. Enhance your day by booking the guided tour or choose to explore the island at your leisure. Start your day with a pickup from your downtown Boston hotel in a minibus and enjoy a smooth transfer to the ferry in Falmouth, Cape Cod. Enjoy snacks and bottled water onboard while browsing the Martha’s Vineyard guidebook as you plan your six hours on the island. After a short ferry ride, disembark on the beautiful island. Admire the picturesque gingerbread cottages of Oak Bluffs and explore the quaint downtown shops of Edgartown. Soak up the views at the Gay Head Cliffs and marvel at the famous lighthouse in the town of Aquinnah. Bike and Jeep rentals are available for purchase, or simply explore the island with public transportation. You will also be provided with a discount card valid at some of the island's restaurants and attractions. After your day at Martha's Vineyard has come to an end, take in the views once more from the ferry before unwinding on your comfortable transfer 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.

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 4th and 5th-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.  See many sights where JAWS was filmed. Enjoy the use of a new sound system and clips from the movie to really enhance the experience.

Boston: Martha's Vineyard Day Trip with Optional Island Tour

4. Boston: Martha's Vineyard Day Trip with Optional Island Tour

Start the tour, with an early morning pick-up at your hotel between 6:45 and 7:30 AM. Take advantage of the complimentary snacks, water, maps, and discount food cards that are included in the vehicle. Arrive at the Martha's Vineyard Steamship Authority Ferry in Woods Hole, MA. Before boarding, there will be time for a spot of shopping or to enjoy breakfast. The vessel departs at 9:30 AM. Take an enjoyable 45-minute ferry ride to Oak Bluffs or Vineyard Haven, Martha's Vineyard. Food and drinks are available on the ferry, at your own expense. Inside air-conditioned seating, as well as outside sun deck seating, is available. There is plenty of room on this vessel to explore and take many pictures. Upon arrival at Martha's Vineyard, spend approximately 6 hours exploring the beautiful island. Guests who have chosen to take the 3-hour island tour will be greeted directly at the ferry dock. Everyone will depart Martha's Vineyard at 3:45 PM on the Steamship Authority Ferry. When you arrive back at Woods Hole, your guide will be waiting to take you back to Boston.

Martha's Vinyard Driving & Walking GPS-Guided Audio Tour

5. Martha's Vinyard Driving & Walking GPS-Guided Audio Tour

Start by downloading the Action Tour Guide app, which will function as your personal tour guide, audio tour, and map. Purchase one tour per car, not per person. Everyone listens together! Note: This 13+mile-long tour covers the essentials of Martha's Vineyard in 2-3 hours. 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. 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.

Oak Bluffs: Martha's Vineyard Scavenger Hunt Experience

6. Oak Bluffs: Martha's Vineyard Scavenger Hunt Experience

Immerse yourself in charming Martha's Vineyard with an interactive scavenger hunt game on your phone in Oak Bluffs. Uncover the area's rich culture and visit influential landmarks like the Flying Horses Carousel, The Lazy Frog, and the Island Alpaca Company, while solving quizzes and puzzles. After learning the rules of the game, begin your adventure by reading the details on your phone and answering riddles and trivia to advance to the next location. Among the many tour stops is the Flying Horses Carousel, the oldest operating platform carousel in the United States. Take in the beauty of Nantucket Sound as you continue your tour, including The Lazy Frog, a historic store located in downtown Oak Bluffs, and the Island Alpaca Company, an alpaca farm sprawling across 19 acres of rolling farmland. Chat with the locals as you explore the region at your own pace.

Oak Bluffs: Martha's Vineyard GPS Smartphone Audio Tour

7. Oak Bluffs: Martha's Vineyard GPS Smartphone Audio Tour

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of Oak Bluffs. Starting in Ocean Park, you’ll follow the coast to Inkwell Beach before heading into the heart of the town. Along the way, you’ll hear its history and discover what makes this island paradise so alluring to everyone from the rich and famous to curious Cape Cod vacationers that come for a day. Around Trinity Park, you’ll see Martha’s Vineyard Camp Meeting Association, its cottage museum, and the Tabernacle in Oak Bluffs where the religious campers came to worship. After heading down Circuit Avenue, where I’ll show you the town’s famous Flying Horses Carousel, our tour will end at the harbor. By the end of this tour, you’ll have the answers to questions like: • How did Martha’s Vineyard get its name? • What is the origin of the famous gingerbread cottages? • Who are some of Oak Bluffs’ most notable African-American cultural icons? • How did Oak Bluffs go from a religious settlement to a secular resort town? • What is the most famous (and delicious) drink on the island, and where do you get it? Whether you’re on the island for only a day, or calling Martha’s Vineyard home for the season, this tour is for anyone who wants to dig into Oak Bluffs’ past and enjoy its present. Allow 60-90 minutes to get the most out of this tour. There are a few places to stop along the way in case you’d like some relief from the sun or to grab a drink or bite to eat.

Other Sightseeing Options in Oak Bluffs

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What people are saying about Oak Bluffs

Overall rating

4.6
(436 reviews)

Fantastic to cram everything in but my recommendation would be to almost spend an extra day in MV. A lot of things were closed or closing but on the flip side far less busy with tourists so a bonus. Tour guide on MV was excellent but it was an early start so could have done without the running commentary on the way to MV to have a snooze!

Jenny was great getting us to the ferry from Boston and back. She kept it fun and lively. The tour on the island was good. it helped to fill in the 3 hours and then still had time to shop in the ferry town as well as 2 other towns. Definitely would recommend just make sure it's not raining. It will make the trip more enjoyable!

Bart was an excellent tour guide. Very knowledgeable local and showed us around Martha’s Vineyard’s most beautiful spots. If you are there just for the day and have never been on the island, I would definitely recommend.

This was a great tour! It’s so nice to have had a local conduct this tour because she knew everything about the island! Loved everything about this tour!

Excellent day trip. Everything went to plan. Jennifer was a superb driver and Matt a wonderful guide with full local knowledge.