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 Tomasini's have worked hard to make Pirate Adventures the long term success story they knew it could be. The crew you see below has made Pirate Adventures into what it is today. The unexpected bonus of working with this extraordinary group of young people has been a wonderful surprise and we are very proud to call them our "crew".
If you get a chance, let our crew know what a great job they do!

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Kelsie "Scuttle" Bailey brings her upbeat attitude to work every day and understands how to get the youngest pirates excited about the trip. Studying to be a pre-school teacher at Frostburg University we know that Scuttle will continue to touch the lives of young children. Scuttle joins us for her fourth summer at Pirate Adventures. |
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Amanda "Chessy" Coale - The trip is never boring with Chessy aboard! Chessy's incredible creative energy and unbelievable work ethic is hard to keep up with. Chessy has just finished her freshman year at James Madison University and we have been lucky enough to have Chessy with us since the age of 14. |
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Meghan "Goldie" Gardiner has a unique natural instinct when working with children and adds her quirky sense of humor to all of her trips. She also keeps Captain Ruby organized! Goldie joins us for her fifth summer and is currently studying elementary education at James Madison University. |
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Francesca "Zulu" Garrett enjoys her role as a pirate and has a great way of getting the kids in on the act. A trip with Zulu is full of surprises and is sure to include a dance party. Zulu is a sophomore at Anne Arundel Community College and is planning on attending Appalachian State College in the fall. Zulu became a pirate last fall and will join us for her first full season this summer. |
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Kate "Poppett" Graham has an imagination that not even a five year old can match. If you end up on a trip with Poppett, Merfairies and nine tentacled octopus become part of the story. Poppett has just completed her junior year at Davidson College and we hope she never loses her connection with the magical side of things.Poppett joins us for her second summer at Pirate Adventures. |
| Caitlin "Pearl" Hargadon is never without her famous smile and she has been a joy to work with. Pearl has a quick sense of humor and can win over even the most skeptical group 10 year olds. Pearl is studying to be a physical therapist at the University of Maryland College Park. Pearl joins us for her fifth summer at Pirate Adventures. | |
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Christopher "Smee" Hendershot - If you are on a 9:30 trip you will most likely see a Pirate Pete performance by Smee. Always the first to volunteer for anything Smee puts his all into everything he does at Pirate Adventures. As Crabby and Ruby's nephew Smee has spent his summers as a Pirate since the age of 10 and will be joining us for his sixth summer. Smee has just finished his sophomere year at Point Pleasant High School in New Jersey. |
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Erin "Sinker" Hendershot brings her sense of humor and a unique sense of fun to every trip she runs. She is also very good at picking on her Aunt Ruby and Uncle Crabby when they are defenseless in front of an audience! Sinker has been with us since the beginning has just completed her senior year of high school at Point Pleasant High School in New Jersey. Sinker will become a full time pirate this year with plans to attend Anne Arundel Community College in the fall. |
| Nastassja "Peggy" Koellein-Dewaele joins us for her third summer at Pirate Adventures. Peggy's imagination and vocabulary add spice to every trip she runs. Her laugh (and she laughs a lot!) is one you won't soon forget. Peggy has just finished her senior year at St. Tim's, she is mulling over her college acceptance letters and will be back for her third season at Pirate Adventures. | |
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Kyle "Rusty" Nicholson - If you have been on a trip with Rusty, you remember it! Rusty is an incredible personality and he gets everybody he sees (on or off the boat) into the act. With an enthusiastic love for kids Rusty has found the ideal job and we are lucky to have found him! Rusty has just finished his senior year at Arundel High School and we can't wait to see what he does next! |
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Josh "Dinghy" Ponatoski showed up on his skateboard at the age of 14 and we couldn't resist the name of Dinghy. Dinghy quickly became our mascott and joins us for his third summer and it has been our pleasure to watch him grow up! Dinghy is currently a junior at Indian Creek School, we're thinking it may be time to change his name.. |
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Vince "Rudder" Thompson joins us for his third summer and will continue to keep the little pirates entranced with his surprising sense of humor. Rudder keeps the little pirates and the crew on their toes, we never know what he is going to say next! Rudder has just completed his senior year at the Severn School and will head to Catholic University in the fall. |
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Jared "Chum" Stricklin - Chum walked into Pirate Adventures four seasons ago and begins his own adventure this summer with a location on the Outer Banks. Chum obtained his Captain's license last summer and became a partner in the Outer Banks arm of Pirate Adventures with Ruby and Crabby this winter. We are sad that he won't be with us in Annapolis this summer, we won't laugh nearly as hard without him, but we are so proud of our Chum! |
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Leslie "Polly" Zucknick shows up for work every day in a good mood! Polly brings her light and positive attitude to all of her trips and does a wonderful job at keeping all of her trips new and fun for the kids. Polly has just completed her sophomore year at Towson University, she is a track star at Towson and is studying to be an Elementary School teacher. Polly joins us for her fourth season. |