Top 10 Things to do Good for Big Groups in Oak Bluffs, Massachusetts (MA)

Ahoy mateys! Join us as we set sail on a pirate's treasure hunt along the shores of beautiful and historic Oak Bluffs on the legendary island of Martha's Vineyard. On our custom pirate ship your kids will dress and talk like a pirate, assemble a treasure map, battle rival pirates with water cannons and hoist sunken treasure from the ocean floor! Once aboard the Sea Gypsy, we must work together to build a treasure map and determine our course. Along the way, we find a message in a bottle and discover that Stinky Pete, the Island’s smelliest pirate, has stolen the keys! We must raise the battle flag, fight off our enemy with water cannons, and steal back the keys to claim our treasure! The voyage culminates as we discover where "X" marks the spot...we must work as a team (heave-ho!) to raise the treasure chest from the ocean as it's heavy with sea water and sparkling booty. Every one of the crew will be rewarded for their efforts and take home their fair share of the loot. There’s singin’, dancin’, and drinkin’ of pirate grog as we sail back to port victorious in our spoils. You’ll be amazed how quickly the Pirate Adventures crew taps into the wonder of your child’s imagination. This wholesome, family-oriented cruise is perfect thing to do on a day trip, vacation, weekend or really just about anytime your are seeking a child-friendly and action-packed bunch of fun while on MV. There is a reason why Pirate Adventures is ranked high on a family’s vacation highlights. This isn’t a performance by actors - this is a highly interactive pirate experience where each of our trained crew makes sure your child is involved and engaged throughout the whole journey. It's a fun, unique, memory-making adventure cruise designed for families by a family (a pirate family of course).

Discover the hot-spots & hidden treasures of Martha's Vineyard on our tour through the island’s six towns—each with a unique history and character. We offer personalized, all island tours, which are designed to be informative and fun for new visitors. Have photographs & videos taken along the way for a keepsake you can have for a lifetime. Relax in our luxurious, air conditioned vans. See where celebrities stay. Stand on various sets of Jaws. Discover a village of gingerbread cottages. Shop the island’s first general store and finest galleries of local art. Climb to the top of lighthouses. View the infamous 200 ft. cliffs of Aquinnah. Learn more about the expansive African American History of the island. Request customized tours for your children. Enjoy a picnic in Menemsha to delight in the freshest seafood on the docks overlooking the harbor- top it off with a complimentary bottle of wine...and more! You're guaranteed to develop a deeper understanding of this magical destination.

This Oak Bluffs beach and surrounding area of colorful gingerbread Victorian houses have strong links to African-American heritage on Martha's Vineyard, dating back to the Revolutionary War. The beach was the setting for a teenage romance movie called "The Inkwell."

Small waves, low dunes and lots of seashells make this narrow, two-mile stretch of public beach popular with families. The beach runs between Oak Bluffs and Edgartown, and is called "Bend-in-the-Road Beach" on the Edgartown side.

Victorian mansions surround this charming Oak Bluffs park.

Join us for a 2.5 hour narrated tour of all six towns, including a mid-tour comfort stop at the beautiful and famous Gay Head cliffs and lighthouse. Along the way you will see beautiful and enchanting island vistas, historic homes, scenes from Jaws, and the Gingerbread cottages of Oak Bluffs. Tour price includes admission to the Martha's Vineyard Museum and the Gay Head lighthouse ($17 value.)

Try your luck at catching the brass ring and winning a free ride on the oldest working carousel in the U.S., which has been enchanting children and adults for over a hundred years. The 20 hand-carved horses on this official historic landmark have real horsehair manes and tails.

OPEN 7 Days, 10 am to 4 pm. $5 pp Entry fee 'til November 1, 2020. Free admission from Nov. 2, 2020 to April 23, 2021. Island Alpaca invites you to bring the family and friends for a unique experience, including a gift shop filled with locally grown garments, and down-on-the-farm furry, fun. Take their self-guided, walking tour to arrive at the 2,400 square foot antique Post & Beam Barn. Get up close with the friendly fluffy alpaca and meet our new babies, over 30 of them, in our very special viewing area. Bring a sample of their fleece harvest home to your family and friends! (Alpaca's are also for sale!) Open daily, 10 to 4 pm. See you at the farm!

We are located right on State Beach at the Little Bridge in Oak Bluffs. Our kayaks are located on the pond side of the beach so you can paddle in Sengekontacket Pond or go under the bridge and out to the Vineyard Sound. We are 1 mile from Oak Bluffs town center. You can reach us by the #13 bus route, and quick and beautiful bike ride, walk from town or there is plenty of parking available at our Little Bridge location. Happy Paddling!