The question I’m asked about most often is about family sailing. The scenario differs only slightly: Usually a parent of teenagers aspires to sail in a family group, but can’t convince the kids to go. Sometimes the parents learned to crew as younger adults and hope to replay the experience. Sometimes a parent took a lesson or two, saw a deal on a 1978 fixer-upper and feels ready to skipper a family boat. 

There are one of two constants: 1. Either the kids were junior sailors and lost interest by the age of 15, or 2. The kids didn’t know that junior sailing was a thing and think that sailing is “so 1970s,” and only about Mom and Dad’s 1970s friends. Either way, the adult skipper wannabe may as well be pulling teeth.

Sometimes the way to solve a problem is to avoid it in the first place, but that takes longer range planning than most families can reasonably do. It is luckier to blindly miss a problem without knowing that it is there at all. That’s what happened to us. 

My wife and I sailed together before we had kids, and as soon as they were infants we slathered on the sunscreen and strapped them into car seats lashed to the stern rail. Later, we lifted toddlers up to swing from the boom or make forts out of berths. We gave the helm to grade schoolers, and then, by the time our daughters were teenagers, they had become talented, contributing members of our racing team. 

The kids are now adults and we’re still sailing together. As I write this, we’re social distancing on a three week all-adult family Covid-cruise, but that is another story. For our kids, it was never a choice to sail or not to sail; it was what the family did. It might seem to you to be regressive—a more traditional, perhaps controlling way of parenting—but I assure you it was not. It felt more like moving in a pack. Furthermore, we can claim no foresight nor grand plan. We happened to have been surrounded by other families for whom the cycle was generations long—sailing passed from grandparent to parents to kids—so it simply seemed to us like the natural thing to do.

The problem is that our happenstance is not compatible to parents of teenagers who hope to start now, so the solution must be different. Try strapping 15-year-old Caleb, with his temporary driver’s license, peach-fuzz goatee, 1,200 Instagram followers and summer crush Angel (with the rose tattoo on her shoulder) into a car seat.

No, we need to look at this problem differently. 

First, let’s consider Caleb’s perspective. The kids in junior sailing programs were all right at first, but they broke into cliques of winners and losers and as the summers passed, it became clear that he was never big or cool enough to be one of the winners. At twelve, he was tired of being dropped off by Mom or Dad to do the same thing in the same boat over and over. He knows that Dad sailed once too, and that was a long time ago, but it wasn’t in dinghies or in an organized program and, from what he can tell, mom wasn’t in the picture at all. Most importantly, his friends aren’t in any of dad’s sailing plans.

Mom and Dad’s perspective is also complex. Mom is keen to try family sailing, but doesn’t have the benefit of years in a junior program or as a member of a crew. She wants to develop her own skills and safety protocols and doesn’t just want to be a naive passenger. Her husband has proposed buying that 1970’s boat, but she fears that it’ll go unused unless she feels confident and Caleb can see something in it.

I see three factors in families who successfully start sailing late:

They set a collective low-key expectation: Sailing might be limited, at first, to hourly jaunts to develop confidence, and is allowed to evolve into whatever format works for everyone. It might one day result in a cruise or weeknight racing, but it could also simply settle as a way to be social outside once a week. This means that Caleb can bring Angel and Angel’s twin sister Maya to take sunset selfies and share adventures with Caleb’s social media followers.

They find a school or a club that has adapted to the family schedule and dynamic and tap its resources: all ages instruction and inclusion on a variety of boats and formats and under the watchful eye of experienced, experientially minded staff, members, curriculum and programs.

They take it at a family pace, slowing down, speeding up or taking detours, as the pack demands.

And in this way, families who start sailing late start from an all new place. It is not so much about convincing the teenager as it is about working out what family sailing will look like when it meets everyone’s needs. Because by the time kids are teenagers, everyone’s needs are different.