There’s going to be a lot of family boating this summer. Professional sporting events have been severely curtailed. Concerts? Amusement parks? Festivals? Hard to imagine. If you thought you were the family’s Chief Entertainment Officer before, there’s a whole new level of responsibility coming at you in Summer 2020.

First, if you’re going boating as a family, then the whole family needs to have fun. Many of you are blessed with spouses and kids who have always shared your passion for the water. They race with you or enjoy cruising, and have the seamanship skills to take the boat out on their own. On the other end of the spectrum, some of you have basically dragged the family out on the water, hoping they will learn through osmosis, your skills, and love, as you try not to yell at them at critical moments.

There is a better way. Your family will have much more fun if they have more knowledge. Typically, that’s best conveyed by someone other than you. Most professional sailing and boating education operations are figuring out ways to keep their instruction going this spring, and these solutions are going to mean either video, smaller class sizes, and thus capacity, or both. This also means DON’T WAIT! Sign up the family for lessons…soon!

Two top-rated schools that have advertised in WindCheck for years are Black Rock Sailing School and Blue Water Sailing School, both of whom have been honored by the American Sailing Association multiple times. They have not advised us of their plans to adapt to the current environment, but we guarantee they are building them.

If you need something more local, you’ll find a comprehensive list of excellent schools at If you know of others, let us know and we’ll post them. There’s another guy we’ve heard about…Joe Cooper. He might be an option! In the meantime, shorthanded racing, especially with family, will be “a thing.”

New “old” concepts are popping up in racing. I suspect we’ll see a lot of rabbit starts this summer. Another idea being tested comes from Adam Loory, a longtime racer on Long Island Sound and skipper of Soulmates. Adam is organizing a doublehanded “pick-up game” to be sailed Saturday, May 9 on Western Long Island Sound as a trial. So far, it looks like fourteen boats will come sail. To maximize social distancing, there will be no race committee. The plan is to use a pursuit start so that the order of finish is the standings. There will be no entry form, no entry fee, no party, and no trophies. No yacht club, sailing association or company is involved — “Especially not UK Sailmakers, where I have been working for 30 years,” Adam said. “It is designed purely as a chance for people to sail and have some competitive fun.”

If it works out, Adam will try to organize some more races on this format and hopefully have a distance race on Memorial Day weekend. But this is all contingent on the first event going well. The course for the May 9 trial will be a simple one that will start at Can “1” northeast of Execution Rocks, head to a mark to the east and then return. “We’ll pick a course that will take about three to four hours for the average boat,” Adam explained. Participating boats range from a Marten 49 rating in the negative 30s to a Frers 33 rating around 114, with most boats rating between 60 and 90. For more information and to join the fun, email Adam at

See you on the water…soon!

Benjamin V. Cesare

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