Start Sailing Now: Meet County Executive Steuart Pittman

In harmony with the world

“I’ve found that sailing on the Bay is a lot like galloping the countryside on a horse. You’re not in complete control, but when you find the perfect balance and tact, you’re in harmony with the world. There’s just enough danger to keep your blood pumping and senses keen, and you feel alive.” ~Steuart Pittman.

When Anne Arundel County Executive Steuart Pittman, who grew up on a farm and professionally trained horses before being elected in 2018, penned these words in his weekly newsletter this summer, we knew he’d be a perfect fit for our Start Sailing Now page. Here he shares more about his experiences learning to sail and owning boats.

Steuart Pittman sailing
County executive Steuart Pittman loves the idea of exploring on a boat. Photo courtesy of Steuart Pittman

Hooked by Take Some Sailing Day in Annapolis

In 2019 I signed my family up for Annapolis Waterfront and Sailing Center’s Take Someone Sailing Day. We were guests on a beautiful sailboat, and it was fantastic. I was immediately drawn in and started thinking about buying a boat for our family. I ended up with an old powerboat that only lasted about a year. Next, I purchased a pontoon boat, which we still own. My wife and two sons really enjoy it. We keep a couple of paddleboards onboard and have a lot of fun.

But I really wanted to sail, so I got myself a Newport 16 sailboat that was built in the 1970s. I paid about $800 for it, including the trailer, and I taught myself to sail on the West River. Since I love exploring, it wasn’t long before I wanted to go further and go overnight. I began to look for a bigger boat and ended up with a MacGregor 26 motor-sailer. I love it! My wife and sons aren’t quite as enthusiastic as I am about sailing, so with this boat when the wind dies, we just pull up the daggerboard, turn on the motor, and off we go! I have had a blast sailing it out of the West River. If the wind is coming from the southeast, it’s a perfect sail out to Thomas Point Shoal Lighthouse or across to Bloody Point and back. 

Back to (sailing) school

This summer, I was planning to take the MacGregor around the Bay for a week in August, but the engine died in June. I tried in vain to fix it myself, but as my vacation week approached, I decided instead to sign up for five days of sailing lessons at Annapolis Sailing School, something that I had been thinking about for a while. I registered for American Sailing Association (ASA) 101 and 103. With three students and an instructor onboard, we sailed three or four different types of boats, starting with the school’s Rainbow fleet and moving to bigger boats later in the week. 

Take Someone Sailing Day 2019
In 2019 the county executive and his family participated in Take Someone Sailing Day, and he was immediatley drawn in. Photo by Al Schreitmueller

What do you most enjoy most about sailing?

I have enjoyed learning a new skill and being successful at it, but it’s more than that. Being on the water and feeling the power of the wind immediately makes me feel like everything is okay. Everything seems to make sense, and I am a part of it all. I also appreciate the ‘machine’ of the boat. I like figuring out how it all works and making the boat go. Then, once everything is all set, I enjoy just relaxing. Finally, I love the idea of exploring on a boat. It’s a way to travel without paying for hotel rooms, restaurants, or plane or train tickets. 

Future sailing plans

I enjoy my MacGregor 26, but I dream about my next boat. Sometime before I’m done with this job, I hope to upgrade to the next level. I imagine owning a boat that I could take to the islands and do some cruising and on which I could get my wife and kids more involved. Before that I’d go back to sailing school for ASA 104, the bareboat cruising certification course.

Any advice for someone who is interested in learning to sail?

Just do it! You can figure out a way. Whether it’s getting an inexpensive boat, taking a sailing class, or going out with a friend, sailing is more accessible than people might think, and the hours that you spend out on the water cost you nothing. We are really, really lucky to live in this county where we can explore the Bay and its rivers and creeks.