Dwyer isn’t exactly new to sailing, although his path to becoming an avid sailor is somewhat unique, as is his approach. “I grew up in Cheshire, Connecticut, only 20 minutes from the water, but somehow sailing was never something I thought about,” says Don. Having lived in the Midwest for 20 years, he and his family returned to Connecticut a few years ago and settled on the shoreline. “We live in Guilford and keep our J/109 Guardian J at Brewers Bruce & Johnson’s Marina in Branford,” says Don, who is enjoying his fourth boat, three of which were purchased in succession over the past three years!

“It’s funny it took so long to become a sailor,” Don continues. “We actually bought a Capri 14.2 in 1989 when we lived here, but then I got transferred. The only time that boat got wet was when it rained trailering it whenever we moved! We finally auctioned it off at a charity event. We didn’t think about becoming sailors until we moved back. My oldest son Doc suggested we learn to sail. We always enjoyed sports together, such as skiing, golf, climbing, running and flying [Don is a co-owner of Guardian Jet, one of the larger corporate jet brokerages in the world, based on the Green in Guilford, CT.] He wanted to sail, so he, my son Chris, my wife Jan and I took a weekend of lessons together. Doc and I bought a Hunter 27 because we thought we needed a boat to accelerate our learning. Doc and I were flight instructors at one point in our careers, and we were amazed at the lack of structure to the learning process. After a weekend of poor instruction, it was basically: buy a boat and have at it.”

Looking for ways to make their learning experience as efficient as possible, Don and Jan signed up for a week at J World in Key West. “When we started, we felt like we had to be proactive in searching solutions for our desired pace of learning,” he explains. “I know now there are a ton of resources out there but it wasn’t apparent or even clearly defined for us when we started.”

“It was great starting the first year with an older boat because with the minimal investment it was okay to bounce it off docks as we all learned. The second year, we bought a Pearson 33.2. It was a great boat, but whenever we raced we’d do well at the start and watch all the other boats walk away from us.”

“Our big leap came when I met [WindCheck Contributing Editor] Joe Cooper at a Safety at Sea seminar. We had sailed for a season, and had just bought the Pearson, and were thinking of racing. Joe came on board to get us up to speed on safety first, then taught us the skills to participate in regattas. Our goal was to get ready for last year’s Block Island Race Week. We trained all spring and early summer with Coop, and competed in the regatta. Coop is still our coach. I consider him a great sailor but more importantly, a gifted teacher, good friend and trusted advisor.” 

After Block Island Race Week last year, we started looking for a boat better suited to racing. The J/109 is perfect for us. I can race with a full crew, and it’s an easy boat for Jan and me to daysail or cruise. A good light wind boat is not a bad idea for our part of the Sound, so we got the 109 just in time for the Vineyard Race last year and we are having a ball with it.”

“When I wanted to get into ocean racing, I joined Essex Yacht Club and was lucky enough to meet Frank Flores, who has done seven or eight Bermuda races on his Alden 44 Checkmate. Frank invited me to race with him to Bermuda. He is a great skipper and program leader. His love and devotion to seamanship is contagious and I have learned tons by being a part of his crew. We trained through the winter and spring, either by working on the boat, sailing Ideal 18s for crew coordination or sailing Checkmate. We were one of the 50 or so boats that pulled out on the day of the race because of the forecast, but the training was one of the best experiences of my life.” 

“Currently, I race with my extended family. We are extremely lucky that they live nearby, and Jan and I are taking full advantage. The racing community is very supportive. We feel welcome everywhere we go. The Wednesday night league in Branford is a ball, and if I have a question there are a bunch of skippers who jump in and help. We have also enlisted the help of North Sails since buying the J/109. Jack Orr [a member of the sales team at North Sails East] has been fantastic in getting the boat to go fast, setting it up, and teaching us how to trim. My only excuse now is my ability!” 

“For me, the most important lesson so far is to be the architect of your experience. If you are open and honest about your experience level, it is amazing how many people in this sport and industry will help,” says Don. “I’m not big on giving advice, but I would say to someone looking for a way to keep doing stuff with the family, racing sailboats is amazing. If I said to the kids, who all have very busy lives, ‘Let’s go sailing Sunday,’ I’m not sure who would show up. But racing means we get together a lot.”

Don recounts, “We had friends visiting from Kansas who did the Essex Rum Challenge with us. I was sitting on the rail with my buddy, who remarked about how much fun I was having. I looked around the boat, and the entire crew was my extended family and friends. That’s the best part!”