Will Keilty and his siblings come from at least three generations of local sailors who have competed on the waters of Lake Ontario and beyond.
All four children of A.J. and Alexandra Keilty will be spending a lot of time on the water once the warmer weather arrives.
William, 15, has the North American and World Championships in Optimist coming up and trains with the Lake Ontario Optimist Team. He’ll be attending the U.S. Championships in New Jersey before completing his season at CORK (Canadian Olympic-training Regatta Kingston) in late August.
Thomas, 13, is in the junior sailing program at KYC, while Annie, 11, will be training with the Lake Ontario Optimist Team (LOOT), a team of young Canadian and American sailors who will train in the western end of Lake Ontario and also compete at CORK.
Seventeen-year-old brother Jack, 17, also a competitive sailor, he will coach at Kingston Yacht Club this summer.
Alexandra said sailing has been in the family’s blood for generations; her grandparents, parents and herself took part in the Junior Sailing program while growing up.
A.J. experienced a different path into the sport of sailing.
“My husband got into sailing because his mom missed registration at a hockey camp. She was desperate to find him something to do in the summer.”
A.J. is also the Wind Athletes Canada Chair which assists athletes to set up fundraising pages to offset costs of competing. The organization was founded by sailor John Curtis of Kingston.
It was a natural progression for the next generation of the Keilty’s to take up the sport.
“The best part about it is we have four kids and they’ve all been able to engage in it in their own way,” Alexandra said in an interview with Tourism Kingston at the Kingston Yacht Club.
Will finished first in the 2025 Canadian Optimist Dinghy championships in Halifax beating out over 100 competitors from Canada and the United States.
In 12 preliminary races, the grade nine student at Kingston Secondary School recorded two firsts, three seconds and third place finishes and won all the races in the final.
It was his third Canadian Optimist Dinghy Association championship, also winning in 2022 and 2023. In 2024, he finished third.
So far, in 2026, he’s taken part in a pair of international events: fourth place out of 351 sailors at the Palamos Optimist Regatta and 7th (out of 408 international sailors) at the Valencia Opti Orange Regatta.
Will started sailing in Kingston when he was just four-years old.
“My Dad and Mom kind of pushed me into sailing and I enjoy it a lot,” he said. “Once I really wanted to race, I moved over to the Nova Scotia Yacht Squadron and started to really focus on racing. I went for a month and trained there that kind of helped accelerate my development.”
In 2024 Will finished second in the class at CORK but missed competing in 2025 because he was competing in the U.S. Championships where he placed fourth.
“My favourite part of sailing has to be the team racing part,” Will said. There are teams of four or three and they’re each trying to get to the finish line the fastest and having the best combination to win. I enjoyed it a lot because you gain so much understanding of how people think by doing team racing because you can see how they approach a situation like rounding a mark to try and push away another team’s boats.
Team races are on short, tight courses and usually held close to shore so spectators can watch.
Two years ago, Will and Jack came in fifth at the U.S. Team Racing Championship and seventh at the World Championships, the best Canada has fared in the event.
The family has also dabbled in a sailors’ clothing line entitled Parker and Bass.
This summer will be Will’s last season racing the dinghy boats in the Optimist class before aging out.
Next season, Will hopes to sail a model 29er boat and in the future would like to sail the 49er boats in the Olympics and/or team up with his brother Jack and sail F50 boats, one of the fastest sailboats on the water depending on wind conditions. It can reach up to 100 kph. “They are kind of like F1’s on the water,” Alexandra said.
From missed hockey registrations to world-class regattas, the Keilty family story is one shaped by wind, water and opportunity. As the next generation carries that legacy forward in their own ways, it is Will who now finds himself at a turning point, wrapping up his final season in the Optimist class with an eye firmly fixed on faster boats, bigger stages and new challenges. Whether racing alongside teammates, learning from his siblings or chasing Olympic-sized dreams, his course is already well set, and like so many Keiltys before him, it begins and continues on the water.
