Looking for a fantastical adventure your child will never forget? You’ll find it aboard the Sea Gypsy, a mock-pirate ship where kids dress up like pirates, troll the waters of the Chesapeake for sunken treasure, battle other ‘pirates’ with water cannons, and engage in other fun and silly sea-worthy activities.

Hosted by Annapolis company Pirate Adventures on the Chesapeake, this family immersion experience is made even more realistic thanks to great costumes for the kids; enthusiastic crew members who make their pint-sized charges shriek and laugh; and phenomenal props including a life-like cannon and, of course, a ship that really looks as though it could belong to a band of pirates. 

How the pirate adventure works

Pirate Adventures on the ChesapeakeArriving 30 minutes before the Sea Gypsy sets sail allows children to prepare for a day of piracy with face/body painting. They’ll strap on eye patches, bandannas, and other pirate essentials to prepare for the big launch. After preparations are complete, the newly adorned crew of young pirates takes to the water for a day full of adventure.

Meanwhile, parents are invited to sit and relax aboard the ship—after, of course, snapping copious photos of their children decked out in full pirate regalia, including curly mustaches, head scarves, a beautiful mermaid costume, and other seaworthy gear. 

Once the ship sets sail, all hands are on deck for fun, music, and pirate games. While patrolling the Chesapeake Bay, the young pirates take their cues from the ship’s fabulous crew members. Just as the young pirates begin to get comfortable, they’re warned not to take their eyes off the horizon. There are other pirates in the area seeking to take over the Sea Gypsy! Water cannons operated by the crew fend off all attacks, allowing the sea Gypsy to sail another day.

After protecting the ship, the Sea Gypsy floats down Annapolis' Ego Alley as fearful onlookers shudder at the sight of the terrifying little pirates. Before setting foot back on dry land, the young pirates are rewarded for their experience at sea with a treasure chest full of stolen booty.

What they do

A trip aboard the Sea Gypsy makes for a great family outing, birthday party or school field trip. Tapping into the big imaginations of these little seafarers, the staff of Pirate Adventures on the Chesapeake knows just how to entertain their audience. 

Pirate Adventures on the Chesapeake is owned and operated by the husband and wife team of Emily and Michael Tomasini, aka Captains Ruby and Crabby. Since 2003 the Tomasinis have worked to make Pirate Adventures the long-term success story it has become. The couple knows that a great pirate adventure is only as fun as its crew members (employees). That’s why they hire an energetic group of responsible and entertaining young men and women—many returning for multiple seasons aboard the Sea Gypsy. They go to great lengths to bring lots of giggles to their little charges.