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Meet Captain Bobby
Bobby, a Baltimore native, grew up fishing and crabbing with his grandfather on Chesapeake Bay. While serving with the US Army in the Middle East, the sand and desert heat found Bobby daydreaming about the cool water he left behind at home. That daydream became a reality in 2015, when Bobby bought a 45-foot Hunter Legend sailboat. The joy of being on the water and feeling the power of the wind is an experience few get to encounter. Bobby wants to invite not only his family and friends aboard, but new friends who are interested in joining our sailing adventures.
Meet Best Mate (1st Mate) Alicia
As the fleet’s COO, Alicia is the backbone of Boat Baltimore. She’s not only the first mate on cruises, she’s Bobby’s “best mate” every other part of the day. Growing up in a small Southern Maryland town on the banks of Chesapeake Bay, Alicia is no stranger to the happiness and tranquility of living a life on the water. This happiness and tranquility emerges during our cruises as she pours glasses of sparkling wine for our guests at sunset and mixes up mimosas for our morning sails.
Meet Captain Luna
Captain Luna Pearl grew up sailing wooden boats out of Long Island, New York. As a third-generation captain, Luna comes from a family lineage of sailors and seafarers, including her great-grandfather, who inspired the character “Capt. Quint” in the movie Jaws.
Luna got her captain’s license at the age of 19 after a gap year spent sailing for nine months from Long Island to Cuba and the Bahamas. She holds a 100-ton USCG Master’s License and captained charter sailboats out of the North Fork of Long Island until moving to Baltimore in 2024. Luna works as a researcher at Johns Hopkins during the day and is also in a program obtaining her master’s degree during the school year.
She enjoys sharing her love of sailing with both old and new friends and looks forward to sharing it with you!
Meet Captain Adam
A Baltimore native, Adam's passion for the water grew from his family, offshore speed boat racing and sailing enthusiasts.
For more than a decade, Adam has been a fixture on racing sailboats in both Baltimore and Annapolis. Whether it's the thrill of racing or the tranquility of a smooth sunset cruise, Adam has always had a deep connection to the Chesapeake.