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Captain Tony Thommasello

USCG 50-ton Master

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I started sailing in high school on a 16-foot fiberglassover-Styrofoam sloop that I carried on a roof rack mounted on my Ford Pinto. Coming home from Deep Creek Lake the roof rack tore loose, the boat crashed onto the route 70 highway (fortunately no one behind) and broke in half. I was able to get both pieces into the car, repair the boat, and continue sailing it for several more years.

When I was in college my family purchased a Santana 26 swing keel sailboat that enabled me to sail around Chesapeake Bay and easily extract myself from grounding episodes. This boat stayed ashore for several years while I got married, built a house, and had two children. Since it required considerable work to maintain, I decided to take up windsurfing so I could stay tuned to apparent wind and be on the water under sail.

Eventually my wife and I found a Beneteau First 375 in Key West at an affordable price, disassembled it, and trucked it to Maryland Marina in Middle River. After several years we purchased our current 2001 Catalina MK42 from its prior owner on the Potomac River. Although I had taken multiple boating courses, I felt this larger boat required more knowledge. So, I pursued and earned my captain's license with a sailing endorsement.

Once I became licensed, I joined CAPCA and enjoyed meeting other captains during our live monthly meetings (I miss those in-person gatherings). During one meeting I was asked by another captain if I was making money with my license. He suggested several services for which one can be paid: delivery, tow boat operation, running a tour boat, and teaching. The notion of teaching was an attractive option because I was already on the faculty at the University of Maryland and had been teaching for many years. I registered for ASA certification with the Kent Island school under Captain David Renoll and began teaching in 2019. I now teach for three schools on the Bay.

I am now retired from my "day job." Teaching sailing is my third career, keeping me active during the sailing season and giving me many days on the water in Annapolis, Havre de Grace, and Chester River. Windspeed Sailing, LLC. is my business offering day sails out of Baltimore, Middle River, Rock Hall, and Annapolis.

A great pleasure is having my family aboard for cruises in the Bay seeking gunkholes for quiet overnights and relaxing days, absorbing the sun while sitting at anchor, paddling around on my kayak or paddleboard, and taking the dinghy ashore for a meal in one of the fine restaurants on the Bay.

It is said that sailing is a way of life. It has certainly taught me many lessons: patience, consideration for others, respect for nature, thoughtful troubleshooting, assuming responsibility for my actions, planning ahead, and being focused on the task at hand. I pray that I will remain healthy, maintain a youthful spirit, and retain the energy needed to continue sailing for many more years.