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Local Sailor Phil Mills Shares Thoughts on Raising Young Sailors

We all say sailing is a great family activity, unless, of course, your family doesn’t like to sail. In our recent podcast with parent Phil Mills, he mentioned some strategies he’s used to help his young kids learn to love it. We wish we’d heard these ideas when our kids were young.

How do kids end up loving sailing?
© 2026 Latitude 38 Media LLC / John

One of the simplest he says he heard from a friend is to make sailing feel special. Phil always brings favorite snacks or treats that the kids do not normally get at home. Sailing becomes a place of special treats.

Another great idea he suggested was to quit while everyone is still having fun. Grown-ups can go out for a day, but Phil reminded us that kids get tired more quickly and head toward a meltdown. His suggestion is to head back to the dock while everyone is having fun and not when the kids are tired, cold, bored or upset. He wants the last memory of the sailing day to be happy and wanting more rather than misery.

Phil is a big believer in keeping it simple and keeping it fun. Head home while everyone is still happy.
Phil is a big believer in keeping it simple and keeping it fun. Head home while everyone is still happy.
© 2026 Latitude 38 Media LLC / John

Phil also presents sailing as a privilege, not an obligation. He likes to tell the kids that sailing is the reward you get for doing your chores or homework or something else. It’s a basic word shift of, “Hey, if you do this thing, you get to go sailing.” That comes with good snacks too.

The last step is giving them independence and control. Let kids sail their own small boat when they are ready. Being the captain of an Opti, El Toro or similar dinghy can create a much stronger sense of freedom, competence and ownership than simply riding along with an adult. Phil saw a completely different look on his son’s face as he solo-sailed into Ayala Cove for his first time.

El Toro sailors
A positive milestone for many kids is the first time skippering a boat on their own.
© 2026 Stockton Sailing Club

We can’t say we were as thoughtful with our ideas on how to help our kids enjoy sailing with us, so we consider ourselves lucky that our family still loves to sail together. That said, we like to do it for fun and also think time in small boats is important. Big boats are intimidating, and the bigger loads and forces make it harder for young kids to be part of the action. When parents bring young kids on big boats, they find themselves saying, “Be careful” or “Watch out” or “Stay away from that” — all words of danger that make sailing sound scary. Small boats make it much easier for both parents and kids to relax and enjoy a sail.

Everyone is different, so there are no foolproof strategies for success, but we thought these all sounded like good ideas and worth a try.

 

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