Welcome aboard the island’s first and only pirate ship! Our brand new 40 ft custom vessel is designed just for kids! Ideally suited for 2-10 year olds, it’s a stage at sea, a safe, magical place for imagination to take over and memories to be made. From beginning to end, the action is non-stop as we transform your kids into our hearty pirate crew. Every new mate gets a pirate name, face-paint, dress up and learns how to talk like a pirate - all before we leave the shore!

Once aboard the Sea Gypsy, we must work together to build 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 will heave - ho a booty-filled chest dripping with sea water and filled with sparking treasure. Every one of the crew will be rewarded and take home their fair share of the bounty. 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 your day trips, vacation, 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 of our trained crew makes sure your child is involved and engaged throughout the whole journey.


  • A 90 minute experience -Approximately 30 minutes on land, 60 minutes at sea

  • Pirate face painting, Pirate dress up, Pirate ID

  • Official pirate training for our new mateys

  • Participating in an action/adventure story at sea

  • Firing real water cannons at attacking pirates

  • Pulling up the sunken treasure and taking home your share of loot

  • A grand-finale pirate celebration dance party

safe, summer memories

Our adventures are custom designed to make your experience a safe one.  Our captains are United States Coast Guard licensed, trained in First Aid and CPR.  The Sea Gypsy is USCG inspected vessel equipped with lifejackets for everyone on board; our little mates safety is our first priority. Our trip is geared for family fun and appropriate for children of all ages. Our ship does not go “out too far” so you will be close to shore for the entire pirate adventure. Our goal is to provide wholesome, safe Summer memories your family will treasure for a lifetime!

We hope to welcome you aboard as we’ll need all the help that we can get… Sail ho!


join our crew!

Pirate Adventures Martha's Vineyard operates from the beautiful waterfront of downtown Oak Bluffs and is easily accessible from all of the major Oak Bluffs ferries and down-Island towns.  We’re sailing Memorial Day through Labor Day. Call (508) 687-2023  or www.mvpirates.com to join our crew today!