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Chester County Press

Cecil County Life: Windward on the Chesapeake

12/16/2025 02:46PM ● By Gabbie Burton
Sailing the Chesapeake [4 Images] Click Any Image To Expand

By Gabbie Burton
Contributing Writer

On a recent assignment for Cecil County Life, I found myself in new waters – literally.

Earlier in the year, when I was told I would be taking a lesson with the BaySail School of Sailing in Havre de Grace, my thought process never extended far beyond, “That sounds like fun.” I’ve been on a few small boats before, though never a sailboat, and I figured my experience would largely be the same, but when I arrived at BaySail and met owner and instructor Jeff Stagnoli, I was more than a little concerned to hear the proceeding questions and talking points:

“Do you get seasick?” 

“Have you been out on a sailboat before?”

I answered “No” to both when I realized that I may have been slightly unprepared to take on this assignment.

Stagnoli and I then moved into the classroom -- where all sailing lessons begin at BaySail – so that he could bring me up to speed on what to expect from my lesson on the Chesapeake Bay. I was told about conditions for the day, still dealing with remnants of a nor’easter, which meant a warning that the wind was on the higher side. This led to another warning about a sailing terminology called heeling.

Heeling, I learned, is when the sailboat leans or tilts on one side in reaction to the wind pushing the sails. Apparently, a sailboat can heel so far as to have one side of the boat’s rails in the water.

“I just wanted to tell you that now so that when we’re out there you know what to expect,” Stagnoli said. “It’s going to feel like the boat is tipping over, but it’s not.”

Quickly, my sailing ignorance turned into anxiety, and I tried to put my worries at bay while Stagnoli taught some of the other basic concepts.

“The wind pulls the sailboat, not pushes it…” he said.

My leg is bouncing uncontrollably.

“The windex will tell you which direction the wind is hitting the boat…” 

I’m biting the insides of my cheek. 

“The jib sail is the front sail…” 

I’m starting to sweat.

Nonetheless, my curiosity and Stagnoli’s assurances prevailed over my worries as we put on our life vests and prepared to board the 33-foot Hunter sailboat. Once on board, I took a look around below deck at the kitchen, beds, and bathroom before taking a seat up top, making sure to locate something sturdy to hold onto, should my heeling nightmare occur.

As we undocked and headed out on to the water, Stagnoli shared that sailing is not his primary career. After a successful career in HVAC, he took a break before becoming a business coach, which remains his current job. When he signed his son up for sailing lessons at BaySail three years ago, the previous owners said that they were selling the business, which prompted Stagnoli and his wife, Nicole to purchase the school.

Since then, Stagnoli has taken on sailing himself while also continuing his business coaching. His daughter, Kristina Witt manages BaySail, whose inventory and staff includes 13 sailboats and nine captains available for rentals and lessons, including classes for beginners. 

“Business consulting is my real job,” Stagnoli said. “This is for fun; it’s not about the money.”


‘It’s all about the boat’


Once we were out on the open water, Stagnoli started opening the sails while directing me to steer the boat. By looking up at the windex - a wind vane blowing above my head showing me where to guide the boat - I turned the wheel to keep us on course while ignoring my private thoughts that told me that I was definitely going to screw up. While steering was definitely a necessary part of the experience, I found the most pleasure in sailing while sitting on the sidelines, letting Stagnoli and his relaxed presence be at the helm.

After Stagnoli and our photographer Jim Coarse got the sails situated, I asked Stagnoli what his favorite part about sailing was. He cut the engine to let the wind do the work, while he shared a story about the previous owner, Rick, who taught him how to sail.

“There was this moment when we were out on one of the smaller boats and the sails were out and it was quiet,” Stagnoli began. “Rick said, ‘Do you get it yet? Just stop and listen. It’s all behind you, and none of it matters right now.’ I still get that feeling almost every time I go out on the boat. Just the simplicity and taking the beauty of the scenery in.”

I could relate immediately to what Stagnoli was saying. On the sailboat, I felt a calmness wash over me and it felt like a pause on reality to just be there, still for a moment, riding on the water. My previous worries were far from my mind as I relaxed into the scenery and embraced the sailing experience.

Eventually on the hour-long sail, I caught myself being so relaxed that I began wishing for more heeling, just to get my premature adrenaline pumping again - something I least expected.

As our sailing experience came to a close, I was both proud of myself and surprised by just how much I enjoyed the experience. I found myself looking forward to the day I could go again, perhaps more adventurously, and hopefully in favorable summer weather.

That day, and seemingly every day, Stagnoli and the entire staff at BaySail School of Sailing succeed in sharing the mission of BaySail School of Sailing.

“I just I want people to get out there, on the water,” he said.

BaySail School of Sailing has repeatedly been honored by the American Sailing Association (ASA) as a “School of the Year” for its wide range of ASA-certified courses from Beginner to Bareboat Charter Certification and is recognized worldwide by sailing professionals and yacht charter companies. It is located at 100 Bourbon Street, Suite D, Have de Grace, Md. 21078. To learn more and register for a course, visit www.baysail.net. or call (410) 939-2869.


To contact Contributing Writer Gabbie Burton, email [email protected].