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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 First Mate Jeny
Originally from Florida, Jeny found her way to Baltimore by way of Alaska nearly twenty years ago—and has called it home ever since. Her love for the city deepened through her experiences learning to sail at the Downtown Sailing Center (DSC), where she immersed herself in all aspects of sailing, from competitive regattas to overnight cruising adventures.
In 2023, Jeny earned her Basic Keelboat Certification from US Sailing, further anchoring her passion and commitment to life on the water.
Whether you’re a seasoned sailor or stepping aboard for the first time, Jeny is excited to share the magic of Baltimore from the deck of Saeda.