I hear you on the outdoors versus video games. My two sons are now in their mid twenties and remain very active in sports/activities. I was fortunate enough to be a primary care provider (worked from home) so I spent alot of time with them as they grew. At that point in their lives, I (right or wrong) decided they were not going to have electronic babysitters. I now believe I should have provided some compromise . . . but we certainly stayed busy.
Back to your sailboat . . . they have a clean design and when I mentioned stiff wind, I seem to remember that those things really pick up speed quickly. In fact, you and your son could spend time waxing and rewaxing the hull so as to make it as friction free as possible. Great thing to do and test. Even if each time the results are not that much you can certainly imagine they are . . .
Personal floatation devices are a must. Hope to read about your adventures later this year.
Steve