THE CAPTAIN: FLINT

Capt’n Flint is an Islander, born and raised in Oak Bluffs and at Dockside Marina.  He has spent his entire life with salt in his hair and splinters in his toes. After a stint as an attorney, Flint could no longer bear the shame of that profession, and opted for a more respectable life as a Sea Dog. Capt'n Flint holds a USCG Certified Master’s License is CPR and First Aid Certified and holds a PhD in Pirate Linguistics.  

THE LADY PEARL

Lady Pearl is the brains of the crew and makes sure all aboard are properly outfiitted, organized and ready to plunder. She is still determining when to use "arrrrr" or "arrrgh," but loves to yell "aye-aye." Mrs. Pearl is always setting course for the next treasure seekin' adventure and has been known to make more than a few of the crew walk the plank!

CORAL

2015-2020

Our first-first mate, Coral was THE original pirate on the Sea Gypsy X and head of the pirates, under Captain Flint. Don't let this pirate's sweet face fool you - she'll plunder like the rest of the scurvy dogs. She's been known to make use of the cannons to keep the pirates in ship-shape.

SCARLETT

2015,2016

Scarlett sailed with Pirate Adventures for two consecutive seasons. Her enchanting singing voice has been known to charm many a merman and sailor alike. Native of the island, Scarlett knows these waters like the back of her hand. Our ship is her stage, but beware: Scarlett is known for stealing other pirates' lines.

BOOTSTRAP

2015

Bootstrap is one of the original pirates from the first year we voyaged in 2015. One day while out fishing off the shore, a large figure floated up to us in the water. We took it to be the a threat and were ready to fight, when a bottle of grog was tossed aboard. This Hawaiian pirate came to us as surprise, and a blessing. Bootstrap is our "good time" pirate, and we think of him often. We always tell the tales of Bootstrap to the new pirates of our crew; there's really no one out there like him.

SHACKLE

2017,2018

Hailing from the Adriatic Seas of Croatia, Shackle washed up on the shores of the Vineyard in the Summer of 2016. At first glance, this pirate is quite intimidating, with luscious dark hair, standing at a staggering 4 anchors tall. However, his actual given name is Shrimp. He is especially known for his patience with the younger pirates (as they often like to use his him as a jungle gym) and his expertise in foam sword duels.

Mako

2019

Here we have our new Rookie of the Year, everybody meet Mako! As fierce as the fastest shark in the ocean, Mako takes no prisoners. She is a fearless pirate, known to jumpship at the first sight of treasure below. Mako is a rootin’ tootin’ good pirate, and we overjoyed to make her part of the crew for her first year aboard the Sea Gypsy X.

HECTOR

2015-2022

Hector is the Pirates of the Caribbean enthusiast in our crew, and part of the original pirate crew back in 2015. In the spirit of Jack Sparrow, Hector made his way to us across the Atlantic Ocean from the Republic of Georgia. Hector quickly became part of the pirate family, with his charming personality and unwavering support for our crew.

RUDDER

2015,2016

Also known as "Wudda" by our crew (and many of the younger pirates still learning their A, B, Seas...), Rudder sailed with us since our first summer in 2015. He's always been our "boat guy," with the most extensive knowledge of all things nautical. The Captain loves Rudder so much that it's been rumored he is betrothed to the Captain's unborn daughter.

SKULLY

2018,2019

Skully can be so silly, but when it comes to treasure this pirate means business. Her warm smile, funny joking, and clumsy nature won over the hearts of our pirate crew, and we were more than happy to have her join our crew in 2018. She loves a good game of pirate tic-tac-toe so make sure to challenge her when you see her on the harbor!

BONES

2018

We love this pirate from our head to our bones! Bones was from a far away land called California. It's a magical place filled with whales and ships, but sadly no pirates. So Bones searched and searched until he found his perfect pirate crew, us! Bones was beloved by our pirate family and grew into the fierce pirate we all know he could be.

HAWKEYE

2015

Hawkeye was the youngest member of the Sea Gypsy family our first summer, and has been known to take a beating from his crew, but always does so with a smile on his face. His quirky and silly personality is adored by all. Hawkeye is also known for lurking around the pirate ship or Dockside, even on his days off!

SKIFF

2017-2021

One day while out on the water, a bold pirate tried to take our pirate ship by force. With nothing but the oar from her skiff, this pirate tried to plunder our whole crew. We liked her moxy, and so Skiff became a part of our crew in 2017. This pirate is a friend to all and one of our hardest working pirates. She has quickly moved up through the ranks and looks forward to pirating every summer!

GUPPY

2016,2017

Aka Young Gup, aka Gup, aka Young Gup Finch, this zany and hysterical pirate was a new addition to the crew our second summer. One day while hauling up the treasure chest from the bottom of the sea, instead of being face-to-face with our bounty, we were looking into the big eyes of this curly-headed pirate at the end of our line. And boy, are we glad we did. Young Gup, although demure in stature, has proved a fierce asset to our crew.

BUBBLES

2017-2019

We bumped into Bubbles in summer of 2017, much like her name, she is a smiling and happy pirate. She swims like a mermaid through the sea and her energy gives her a great advantage on our adventures. If you see Bubbles give her a nice "AHOY!" and you're sure to hear one back.

JETTY

2018,2019

Are you ready to meet Jetty? Earlier last summer, as we were leaving on one of our adventures, we heard a small pirate's voice calling out to us from the Jetty. When we didn't respond, she dove off and forced her way onto the boat. We were so impressed we took her in on the spot, and so Jetty was born a Sea Gypsy!