All a board! There’s nothing like a little dinghy to test one’s sailing skills, a statement especially true when you start loading up the passengers.

A love of sailing is a legacy that can be passed from one generation to the next, a bond that grows stronger over the years, as hours spent on the water create lasting memories and stories to be handed down. In my case, I believe that legacy may have skipped a generation or two, dying out somewhere around Prohibition, when my great-grandfather ran rum from Bermuda to the mainland in a sleek wooden ketch. His colorful, if shady, adventures seem to have eliminated the sailing bug in my father's branch of the family. My mother's only experience with sailing came from Friday afternoon lessons in a very rainy season, where every class was spent indoors, tying knots. Nonetheless, I developed an interest in sailing at a young age, and one summer, my mother enrolled my brother and me in sailing lessons at a local lake.

The lake where I learned was narrow and the winds generally light but flukey, which didn't make for any hair-raising adventures, but did develop my skills in light-air, upwind sailing. My friends and I, once we'd passed the initial competency test, would take out the Laser and practice capsizing. Somewhere in there, the fundamentals sank in, but my main memories of that time involve a feeling of freedom, and a lot of laughter. The frequent minor mishaps we experienced taught us problem-solving skills and further entrenched the lessons we'd need later on.

I thought of those times recently when my friend Sue reported that she'd signed up her son Cameron for sailing lessons. He's five years old, and I commented on how exciting it was that he'd be out on the water at such a young age, and asked if she thought he'd be nervous. "I don't think so," she answered, "Plus, I'll be there—I'm taking the lessons with him." I'd never taken lessons with a parent; by the time I was sailing, I was at an age where my mother's presence would have caused me to die of embarrassment, but Sue was jumping in early enough, and I looked forward to reports on the experience.

She called to check in after the first lesson. "It went well," she stated, then added that when the instructor solicited questions, Cameron had asked, "If Elvis invented rock and roll, who invented opera?" (Captain Rob now knows not to say "Go ahead, ask me anything.") The summer went on, and each lesson presented different challenges, and I could tell, each time I talked to her, how happy she was to be part of the experience. The lessons afforded the opportunity to solve problems together and share successes while learning the fundamental principles of sailing that can foster a lifelong love of being on the water.

Getting an early start sailing not only hones the skills, but means being able to spend more time pursuing the thing you love.

If you love sailing, it's easy to get caught up in enthusiasm and a wish to pass on the love of the sport. It's important also to consider the matter from the child's point of view. It may be unimaginable to you, but some kids may not be ready to take on the challenge of learning to sail. Sailing requires attention to detail and discipline, and if a child is too young or inattentive, the experience won't be enjoyable for anyone. My friend Sue was fortunate, in that her son shared her interest in sailing and expressed a desire to learn, but that's not always the case. Plan an afternoon trip for you and the child, and see how he reacts to the experience. You can help the process by responding patiently to questions, identifying the various parts of the boat, and pointing out landmarks. A short trip will give you enough information to easily gauge the child's interest for the subject, and if you make it appealing for him to participate, you can help develop that interest. Showing respect for your child's reaction to sailing will help you in the long run. No one wants to be forced to enjoy an activity.

Many people teach their children to sail with excellent results, but there are some benefits to enrolling yourself in lessons along with your child. First, depending on your own skill level, the course can act as a refresher for you. If it's been a while since you were at the tiller, it never hurts to brush up on the basics. Second, the other students in the class are a peer group for the child, creating a safe environment where he or she can learn to work as a team. Having an instructor present can relieve some parental pressure—you and your child will be free to be students, and learn together.

There are a number of questions to sleuth out before signing up for just any old sailing school.

Many organizations offer parent-child sailing lessons, and a little research should turn up an appropriate venue for you. Some of the things to look for when researching lessons are: