Staying on track to a lifetime of sailing

Published on May 8th, 2022

Since this article by Chris Caswell was originally published June 2018 in Sailing Magazine, the landscape for youth sports remains a concern. The eagerness to parlay athletics into some kind of payday, despite the monumental odds against it, hasn’t significantly hastened the parental push.

For youth sailing, the best example of progress is the ‘Un-Regatta‘ format in the O’pen Skiff Class which states:

• Results are not nearly as important as everyone having a good time sailing.
• Capsizes, boat handling challenges, speed, and fun will be required.
• If you are a hard-core racer with rule book in hand, this event may not be for you.

As summer approaches and youth sailing activities increase, consider what’s most important: a small percentage at the top of the triangle earning trophies or the base of the triangle embraceing a lifelong recreation. As you consider that, here’s Caswell’s commentary:


I have a few rants that pop up from time to time, so consider yourself warned. This is going to be one of them.

One of my rants has been the late, great, America’s Cup, which sadly is the empty shell of a once-epic event that no longer relates to today’s sailors. I don’t beat that dead horse anymore, because I simply don’t care.

But I care about today’s kids, who seem to be living in a world populated by helicopter parents and a sailing lifestyle best described as a “trophy culture.” Winning is everything.

I was at a yacht club recently, watching the junior sailing program with coaches in chase boats yelling at the kids going through drills. It had started before I arrived and was going when I left, and I was saddened by the sheer monotony of it.

I thought back to learning to sail on California’s Alamitos Bay in a community program where the essence of the summer sailing program was to have fun. There were blackboard talks about both sailing and racing techniques, but then we were turned loose in our 8-footers to go have fun.

Fun meant water fights or piling a bunch of kids in your boat to go to a sandbar or just sailing companionably with others “going nowhere and doing nothing.”

While the kids I saw recently could bang off perfect roll tacks, there wasn’t much joy. There were no peals of laughter, no shouts to friends, no splashing. Just drill, drill, drill.

When I look back at the now-grown kids from that summer sailing program so many years ago, the vast majority of them are still sailing. Like me, some went on to a lifetime of collecting trophies, while others chose just to sail and cruise. But sailing stuck to us.

Winning is not a bad thing and, in fact, kids like to win. But when winning becomes more important than being out playing, it sends the wrong message. Rather than forcing your kids into a program to win trophies and finish first, perhaps you should encourage them to have fun and make friends.

And splash some water.

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