Despite growing up in Baltimore, Bobby LaPin’s love of boating was born in one of the driest places on Earth.
The Army veteran, now known locally as Captain Bobby, was working in Iraq as a contractor in 2015 when he was struck by a crazy idea at the most inopportune of times.
“There was an attack on the base that I was on, and I’m sitting in one of these bunkers, looking through this magazine called Cruising World, and I said to myself, ‘If I make it out of Iraq, I’m going to buy a boat and live on it,” says the 46-year-old Upper Fells resident today.
He did, and he did. A decade later, LaPin and his wife, Alicia, run Boat Baltimore, a private sailboat charter on their 1985 Hunter Legend 45, SAEDA. The 47-foot vessel has two cabins, a living room, a galley, and an office, but most of the people who climb aboard for 90-minute sunset cruises prefer to lounge above deck.
Now, LaPin may be known as much for his social media presence as his nautical chops. His Instagram page, @SailLocal, has more than 74,000 followers. He posts irreverent and amusing material on everything from the history of Baltimore to his foray into accidental farming.
In fact, he’s become somewhat of a citizen journalist, delving into street preservation in Fells Point, the prevalence of urban deer populations, and incidents like the June oil spill in the harbor.
But the online world, of course, is not entirely picturesque. When he posted a video criticizing President Trump’s plan to spend $45 million on a military parade, he was besieged by trolls and lost more than a thousand followers. Yet he was undeterred.
“I’m very open about being a non-MAGA veteran,” says LaPin. “We got a lot of business from that.”
Since 2022, Boat Baltimore has differentiated itself with affordable sales and even programs like “Elope on a Boat.” LaPin, who became an ordained minister online, has married countless couples on the open water.
“When I was a kid growing up in Baltimore, I remember fishing with my grandpa and looking at these sailboats go by and thinking to myself, ‘That’s for rich people,’” he says. “My whole goal is to make sailing more accessible to everyone.”
When did you get your captain’s license?
In 2022, when everybody was still drinking because of COVID, I wanted to make it productive, and I went and got my captain’s license. It was just going to be a side thing, but we got so popular with Instagram that by 2023, I quit my job and now run the boat business full-time.
What’s the meaning behind the name of your boat, SAEDA?
It stands for Subversion and Espionage Directed Against the United States Army. When I was a counterintelligence agent in the Army, one of the programs that we administered was this thing called SAEDA. Basically, we would give briefings to soldiers who were either going abroad, going on deployment, coming back from deployment, going out for the weekend, whatever. It was, “Hey, if you see anything that could be suspicious, people messing with the equipment, if you hear your fellow soldier saying that they like Putin more than America, come and let us know.”
When I renamed the boat, I realized the only reason I have a boat is because of that short time I did in Iraq as a contractor. And the only reason I got that job was because of the skillset the Army gave me. So I wanted to honor the Army by naming the boat something special. I had to call the Army to get approval to use that name. It’s the only boat in the entire world named SAEDA.
Do you still live aboard her?
No. When I met my wife, she said I couldn’t do that anymore. So we live in Upper Fells, and the boat is down in Baltimore Peninsula. We’re the only locally owned and operated charter business in Baltimore.
When did you dive into social media?
I posted a video in 2023. It was real simple. I’m an old dude, I didn’t know how social media worked, right? So in the very beginning, I would just have videos and say, “Hey, book a cruise.” Eventually, it kind of went into me showing off the sunset and different parts of the city. In this one video, I said, “A lot of people don’t believe when they see our videos that this is Baltimore, but you can see behind me Fort McHenry, the city of Baltimore, and look at that sunset.”
That first video, I think, went over 100,000 views. And we got a lot of hate comments. “Is that a body in the water?” “This isn’t in Baltimore, this is the county—you’re faking.” And I started clapping back really hard. And from there, man, our Instagram just sort of grew quickly, organically.
Where do you sail and what do people do while they’re on the boat?
Well, it’s a sailboat, so we kind of just go wherever the wind takes us. We start from Baltimore Peninsula at the Port Covington Marina. And we generally sail out the Middle Branch [River] toward the Key Bridge, or what’s left of it. If the wind is blowing out from the [Chesapeake] Bay, we can make a run down into the Inner Harbor. But most of our cruises are in the outer harbor because it’s cooler out there. Mostly, as soon as you pull the sails out, people go up front in those adjustable chairs with their drinks and their charcuterie. That’s normally what they want to do—just chill and relax and just get away from life for a little bit.
How did “Elope on a Boat” start?
My wife and I met online during COVID, like a lot of couples did. And we decided quickly that we loved each other, and we wanted to get married. So instead of having a wedding where the old people might die because of COVID, we eloped. And when we started the business, somebody reached out to us and asked if they could get married on the boat. And since I was ordained, I just randomly said, “Yeah.” My wife’s idea was to have a program called “Elope on a Boat.” I marry two to three couples per week now. I’ve married over 50 couples in the city of Baltimore on my boat in the harbor, which I love.
Do people ever propose on the boat?
Yeah. That’s almost a near weekly thing. I would say the number one thing that happens on our boat are anniversaries and birthdays. Number two would be girls’ night out. Almost once a day, there’s a cruise with a bunch of ladies trying to get away. The third most popular thing is engagements. And the fourth is elopements.
What’s so magical about being on a boat? Why do people love it so much?
We meet most people in the parking lot at the marina. [In the summer,] we’re all hot. And they’ve just gone through traffic to get there. And then we get on the boat, we pull off the sails, and when we get into the open harbor, the temperature drops 15 degrees and there’s a constant breeze. People just smile. They get into their music. They bob their heads. They sip on their drinks. And at the end of the day, it’s like they just forget about life for a while. They find the beauty of it all. I don’t know, man. I think at the end of the day, they just find peace, and they find it here in Baltimore.