Sail With Friends: How Racing Built My Strongest Friendships

Most of my posts here have been about skiing adventures. This time, I want to take a detour and share something from my summer sport of choice—sailboat racing—and the friendships that have come from it.

Over 40 years ago, I began racing small sailboats on Lake Minnetonka. The boat I learned on is called a scow—a flat-bottomed boat with a rounded bow, typically sailed tipped over on its side. Scows don’t have a keel, so when you make a mistake, the boat (and sometimes you) can end up in the water.

At first, I got into sailing as a favor to my dad. I didn’t play hockey like he did—what a mistake that was, I thought at the time—so maybe I could make it up to him by trying a different sport he loved.

In the world of scow racing, most people start as kids. By the time they’re teenagers, they’re often incredibly skilled. I, on the other hand, didn’t start until I was about 21—and I had no idea what I was doing. I finished dead last in race after race. But I loved it. Something about the sport pulled me in, and just like skiing, sailing became a lifelong pursuit.

Here in the Midwest, scow racing is primarily a club sport. For those who want more competition, there are regattas, where the competition is deeper and the camaraderie even stronger. These events range from regional races to national championships—and many of the top competitors are from right here in Minnesota, including a few from my own clubs in the past.

One of the best parts of sailing isn’t just the racing—it’s the people. When you sail every weekend with the same group, friendships form naturally. And when you start traveling together for regattas, those friendships deepen. You see the same faces season after season, and year after year. Lifelong friendships form over shared meals, morning rigging sessions, and late-night stories told over drinks.

It’s not unusual to stay in another sailor’s home when visiting for a regatta. There’s a generosity and kinship in this community that’s hard to describe unless you’ve experienced it. Many of my strongest friendships in life have come from sailing.

Take my friend Charlie Hurd, for example—a fellow sailor and skier. Last winter, we organized a ski trip to Grand Targhee with around 30 friends. We blended people from different sailing circles and even added some of Charlie’s college friends. The skiing was phenomenal, but what everyone kept saying was: “The best part was just hanging out together.”

Another great example of sailing-born friendship: the Flood family from Lake Okoboji. Years ago, Jimmy and Pat Flood came to race on Minnetonka and stayed with us—Jimmy’s family and dog included. Every day, we boated together to the regatta site, raced, and laughed late into the evening. Jimmy has since scaled back his sailing, but Pat is still active, and our friendship has only grown stronger.

A few years ago, while staying at Pat’s cabin during a regatta, his sister Joan hosted a wonderful dinner for us and other members of the Flood clan. Just last weekend, I was back again—this time staying with Pat, his wife Betsy, and daughter Kathleen. At this point, I may be inching toward "outlaw" status in their family.

This past weekend happened to be a Flood family reunion—Kathleen and her twin brother Mike were celebrating a milestone birthday. I was able to crash the first night at a local tavern and even recorded a quick video of Jimmy and Pat saying hello to my wife Jackie, who couldn’t be there.

Back home, I sail with the Upper Minnetonka Yacht Club, which also runs a program called Westonka Sailing, whose motto says it all: “Sail with friends.” That’s been true for me in every sense. The racing is thrilling, the lakes are beautiful—but it’s the friendships I’ve made that have given sailing its deepest meaning.