Steuart Pittman on the Sailing School

August 10, 2023

Dear Neighbor,

We all need a break from politics and governing, right? That’s what I’m getting this week in the form of a vacation. But instead of going to the beach or the mountains or doing farm chores, I’ve spent the last five days as a student.

That’s right. I signed up for the two-day Basic Keelboat 101 and the three-day Basic Coastal Cruising 103 courses back-to-back at Annapolis Sailing School, and I’m glad I did.

When you grow up on a farm, there’s not a lot of time to be on the water. I was drawn to animals as a kid – gerbils, toads, dogs, and horses – and made my living training horses before running for office.

Being County Executive doesn’t allow time for horses, so I completely extricated myself from that world. But something was missing.

In 2019, I signed my family up for Annapolis Waterfront and Sailing Center’s Take Someone Sailing Day, and we were “someones.” Out on the Bay, under the sails, and feeling the power of nature’s forces, I found what was missing.

Since that sail, I’ve taken every opportunity I could find to get on the water: kayaking, paddle boarding, pontoon boating, sailing on a 16-foot trailerable boat that I found online for $800, and most recently on a 26-foot trailerable sail boat that is currently on life support at the boat hospital. “You get what you pay for,” my wife always tells me.

What I’ve found is 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.

Suffice it to say that sailing school didn’t feel like school. Yes, I had to read two text books, and I even had to pass two tests, which I’m proud (and relieved) to say that I aced. But most of the time was on the boats with two other students and either Phil or Walt, both of whom were as seasoned as Popeye and committed to teaching. I learned a ton and am closer to the balance and tact that we strive for.

The Annapolis Sailing School has it all, from inexpensive weekday rentals, to the Keelboat Club, to every level of course offerings, and they have the most scenic beach on the Bay at the entrance to the Back Creek.

But they’re not the only game in town. Anne Arundel County’s maritime industry is chock-full of opportunities to get us on the water, whether you’re up for an hour on the Harbor Queen, a floating exercise machine like a kayak or rowboat, or a million dollar yacht, there’s a business here to serve you.

And join us for our next Anne Arundel County River Days, Sunday August 27 from 10-2 at Quiet Waters Park!

Until next week…

Steuart Pittman

Anne Arundel County Executive

Registration for our second River Days Festival is now open! Visit to join us on August 27th 10:00AM – 2:00PM at Quiet Waters Park to celebrate our county’s rivers.
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River Days is a free event with fun activities for the whole family, including games, live music, food trucks, face painting, crafts, kayak rentals, boat rides, and more. Click the button above to learn more and RSVP today.
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