The last time Pirate Adventures on the Chesapeake, a pirate-themed boat charter for kids in Annapolis, opened for spring break was in 2017. Eight years later, the attraction plans to do the same, setting sail on April 19.

According to owners and operators Emily and Mike Tomasini, opening for spring break in the 2017 season helped them break their attendance record — nearly 650 trips throughout the season. However, poor weather, Easter dates, staff availability, and early spring breaks have not made it possible since then. This year, they are hoping to break their record again.

When kids arrive, they get their faces painted, get dressed up in pirate gear, and hit the water. The boat follows a story and a treasure map, run by the couple’s high school and college-aged staff, who dress up and talk like pirates to sell the atmosphere.

“They tend to be outgoing more than theatrical, and they just embrace the lifestyle, being outside,” Tomasini said. “Most of them don’t wear shoes, you know? They love kids. They love being here. It takes a certain personality for sure, and we’ve got them.”

The Tomasinis don’t provide a script for the employees and are open to trying out their ideas to spice up the cruises.

“That’s what makes it really fun to work with young people; they come in with some crazy ideas, and sometimes we’re just crazy enough to let them try it,” she said. “It’s always a work in progress.”

The attraction, located by the water on Third Street in Annapolis, opened for its first season in 2003.

It started as an idea from Emily Tomasini, who had just graduated from college with a teaching degree but was not yet ready to enter the classroom. She and her husband had just visited Cape Cod and became entranced by a pirate-themed charter cruise for kids there. They contacted the owner, who rented them a boat. The couple ultimately decided that Annapolis and its seaside culture were a perfect spot for their business.

This year will feature a new “Pirate Princess Cruise,” as well as charity-focused “give back” days for the nonprofit PlayAnnapolis, which helps less fortunate area children become involved in sports. Tickets on those days are less expensive. Guests can donate money in addition to the ticket prices; a portion of ticket sales and donations will be matched by the attraction.

The couple said they like to keep their operation modest-sized, believing that having a smaller number of kids on the boat creates a personalized experience. The staff can get to know the passengers, which the couple feels would be impossible if they used a larger boat.

The attraction welcomes walk-ups but recommends calling ahead to make sure there’s space.

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