An enthusiastic member of Cedar Point Yacht Club, Storm Trysail Club and Cruising Club of America, Deanna Polizzo has logged over 25,000 nautical miles.

“I grew up in Milford, Connecticut but didn’t start sailing until my late 30s,” says Deanna, who lives in Fairfield. “I was invited for a daysail on the boat of a client and good friend on a sunny Sunday afternoon on Long Island Sound. When he asked if I wanted to take the helm, I said yes and was hooked.”

“I’ve been fortunate to learn from many great sailors. Mark Ellman, first and foremost, introduced me to sailing and to Will Donelan, Mark’s doublehanded partner for many years, a very patient teacher. They taught me about ocean racing, safety, navigation, and more. The late Chris Wentz, sailmaker and naval architect, taught me so much about sail trim. Several patient friends have answered my never-ending stream of questions, but those guys gave me my start.”

“Having started late, I felt I needed to make up for lost time. I dove into it, sailing six days a week with anyone that would have me on board! I was doing deliveries to Maine, Annapolis, Halifax, Newport and Bermuda within a few years of setting foot on a sailboat. It was a steep learning curve with immense challenges. I learned by doing, becoming proficient at driving in ocean waves, trimming sails, working the foredeck, navigating, making repairs, and having to do all of it at night.”

“My first race was a Stratford Shoal in 2014, then I started doing Can One racing. My first trophy wasn’t until the City Island Yacht Club Distance Race in 2015, on a Beneteau 42s7. We took first in our class and first in fleet, setting an expectation for hardware.”

“I’ve done two Newport Bermuda Races (taking a third in class as a watch captain), seven Around Long Island Regattas (including second overall as a watch captain), nine Block Island Races, nine Vineyard Races, an Annapolis to Newport Race and a Marblehead to Halifax Race. I became a Newport Bermuda Race safety inspector and an STC Safety-at-Sea instructor. I’ve been part of the SAS seminars for about ten years. According to Kelly Robinson, chair of STC’s on-the-water training, I was the club’s first female head instructor.”

“I have a passion for training and furthering women in sailing. Knowing how difficult it was to break, I want to help make that path easier for women joining the sailing community. Last year, Suzy Bradford, Heather Shultes and I approached the STC flag officers and Commodore about starting the Women’s Committee. With resounding support, we launched it with a mission that includes promoting and supporting women in sailing; empowering women to take more leadership roles on boats, including ownership; educating and providing opportunities for women to expand and practice sailing skills; and growing the female STC membership.”

“I proposed a trophy to be awarded to a woman at Block Island Race Week. The Elmina Trophy is awarded for the best performance by a woman skipper or majority woman crew. It was awarded for the first time in 2023. I’m working to create a perpetual trophy awarded at the STC annual meeting to a female member that has been exemplary in women’s sailing and furthering women in the sport.”

“Most of my sea stories are about great people and winning trophies,” says Deanna, “but the most memorable experiences happened on my six Bermuda returns. Those taught me that Gulf Stream weather can be fickle, even experienced sailors get seasick, be prepared for the unexpected as hardware failures happen, inexperienced crew can be dangerous, having a buddy ship is a good idea, and if something’s going to go wrong it’ll most likely happen at night.”

“I enjoy cruising and have done several with the CCA and NYYC, mostly to points north through the islands off Massachusetts up to Maine, Nova Scotia and Newfoundland, and I’m looking forward to CCA and NYYC cruises this spring and summer.”

“My passion for sailing began as a way to get my mind off work and make new friends, and I’ve found that the challenges, friendships, bonding and learning experiences make me better in all aspects of my life. I started my own commercial real estate company almost a decade ago, and am fortunate to have met many sailors in my industry and entrepreneurs in other fields. We share information and support, both in sailing and our careers. Ocean sailing builds a special kind of trust formed over days at sea. I’m always amazed at the depth of conversations and support that happens at the rail.”

Deanna’s planning adventure to include Europe, an Atlantic crossing, and the Caribbean. “I’m starting a blog to document my experiences, and I hope it’ll be inspirational to other women and informative regarding everything from provisioning to navigation and repairs, safety aspects, and I’ll be sharing lessons learned along the way starting early this year at”

“I’ve sailed on a variety of boats and am always learning about systems, navigation, sail trim, rigging, and people. I’ve long referred to my time sailing as spending time with ‘Dr. Waters’ as it allows me to recharge and requires me to be mentally present and always at the top of my game. I consider myself incredibly blessed to have found something I’m passionate about that has contributed so much to my life.” ■

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