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From Army counterintelligence to harbor captain: Baltimore veteran sails into new mission

‘Sail Local’: Baltimore veteran turns service and passion into charter boat business
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BALTIMORE — When it comes to starting a business, passion is often the driving force.

WATCH: Baltimore veteran sails into new mission

Baltimore veteran sails into new mission

For one Baltimore veteran, that passion began with a magazine, a promise, and a whole lot of determination.

On the waters of the Patapsco River, Captain Bobby LaPin isn’t just charting a course — he’s living out a promise he made to himself years ago.

“I said to myself, if I get out of here alive, I'm going to go back home. I'm going to buy a sailboat and I'm going to live on it. And right over there is that sailboat,” LaPin said, pointing proudly toward the dock.Bobby served 5 and a half years in the United States Army as a Counterintelligence Special Agent — known as a 97 Bravo — stationed in Korea during 9/11. He says three things saved his life: his mom, Mount Saint Joseph High School, and the U.S. Army.

While overseas, he flipped through a copy of Cruising World magazine — and a dream began to take shape.

In 2022, that dream became Sail Local, a Baltimore veteran-owned business offering charter boat tours along the city’s scenic harbor and waterways.

“I don't think people realize how rare it is to have veteran-owned businesses… when you get out, starting a business and serving your community just seems like the next, you know, logical step,” LaPin said.For Bobby, Sail Local Baltimore is about more than sailing — it’s about connection. He says he draws on his counterintelligence training to learn about his passengers and make every trip memorable.

He and his wife — his first mate, co-captain, and social media manager — have built a loyal following online, showing off the beauty of the harbor and the joy of sailing.

“Opening up a business in the city that I love and that comes across to the customers, I think has made the world of difference… and the customers make the biggest difference to us,” LaPin said.LaPin also believes that sailing can improve mental health, bringing a sense of calm and peace to those on board.

“There's a peace to sailing… and that's why so many different organizations that deal with mental health use sailing as a tool to try to calm people down,” he said.He encourages people to support local, small, and veteran-owned businesses instead of large corporations.

From counterintelligence to the captain’s chair, Captain Bobby LaPin is still serving — this time, one sail at a time.