By Ben Cesare

© Mary Alice Fisher/

A great amount has been written about making sailing more fun for kids so as to keep them in the sport long term. We all know the reasons…the structure and competition (and arms race) of racing is not for every kid, helicopter parenting, competition for time with other sports and activities, and of course the “dreaded digital” are all regularly cited as problems.

Sailing instructors know this all too well! They have been answering the “Are we going sailing today?” (code for “Can we just swim at the dock or play sponge tag?”) question since Week 2. And they know that their job is to get the kids out on the water…that is the whole point.

Now here comes August. The big race weeks are wrapping up or over, most of the championships are done except for perhaps the intramural club champs, and in many places, the breeze is dropping out rapidly and the attendance is getting spottier due to family vacations. Yes, there are plenty of cool non-sailing events in August and yes, you should get your kids to them! But for many there will be some long days and the instructors are tired. It’s time to get creative to end the season strong!

We have spent some time talking to those who have had success: instructors, industry pros, and volunteer parents/program chairs, to come up with a quick list of things to try in August…the dog days. Even if your instructors already know all of these, at least you will know what your kids mean when they tell you what they did at sailing today.


Scavenger Hunt, mooring version

– Tie clues, written on a piece of sailcloth or other waterproof material, to empty moorings or race marks. Assign the kids, ideally two or more per boat, to sail to their assigned mooring to get their first clue. They then have to sail to the rest in order (to avoid traffic jams at marks) to get all the clues. The answer can be a simple letter jumble to form a word. Winners get candy, of course! (Hey, it works.)


Ultimate Sailing Frisbee

– Instructors create a big rectangle (a field) with marks with the long side being 90 degrees to the wind. Teams (say it’s four Optis per team with multiple kids in each boat, but it could be any combo of boats and kids) have to start behind their respective sides. An instructor in a coach boat has the Frisbee in the middle of the rectangle and provides a quick countdown sequence to a start where the kids can reach in from their respective sides. The first boat to get to the coach gets the Frisbee and tries to sail across the opponents’ end “line,” or more likely, pass to a teammate to sail it across. But they have to “pass” the Frisbee right away if one of the opposing team gets close enough to throw water on them with a bailer. (Obviously, some officiating by the instructor will be required.) If the kids are clever and maybe a little strategy has been discussed in advance, one kid will sail straight for the end zone and be ready to receive a pass to win. You can adjust the size of the field to accommodate wind and skill levels. Right of way rules apply, and no bumper boats. Switching sides to have starboard advantage will be a must for round two!


© Mary Alice Fisher/



– OK, everyone knows this one and the kids love it. It’s a game that has many names…one being Bumper Boats! So for true Pirating fun, there might be some minor contact as the kids try to take over, de-rig and flip over their victims’ boats. So obviously, Optis and 420s are not a good choice. But RS Fevas, O’Pen BICs, Sunfish and Lasers work just fine with an appropriate amount of instructor admonishment: You have to swim to your victim’s boat, no boat-to-boat boarding, etc.!


Big Destination Picnic Cruise!

– Make the kids plan and organize a complete picnic, including the destination, how long it will take to get there (wind and tide factored in for the anticipated day), what to bring for food and beverages, and how the boats will be anchored or beached for the event. All of this seems pretty obvious but the reality is, just like some parents, the instructors often handle big chunks of these tasks or well-intentioned volunteers will bring everything along in the family outboard. The point of this is to make the kids do as much as possible themselves. Does the big cooler fit in a 420? Should we cook hot dogs? How will we anchor the boats without banging them up, and what do we do when the tide goes out during our cookout? Again, instructors do this activity regularly but very few make the kids handle the details that come up as a matter of course.

All of these are meant to help the kids learn seamanship with a different bent than windward-leewards or tacking on the whistle. There are tons more but if you ran each of these twice, that would fill eight days in August and leave them smiling. Of course, acknowledging all of this at the awards ceremony will go a long way to burn it into their memories. For proof, check out Scott MacLeod’s missive to WindCheck in our March 2019 issue in the Letters section

Previous Article