Teaching Sailing: How Reflective Practice Shapes Better Instructors and Safer Sailors
Teaching sailing requires the instructor to reflect on their practice and revise regularly, sometimes even instantly. This week, I taught Elements of Sail II at WoodenBoat School in Brooklin, Maine. Eleven students were enrolled in the class that is all about honing fundamental sailing skills. Sail, sail, sail is the goal. Our students came in with wishes of their own. The most-often mentioned goals were gaining confidence in their sailing ability and being safe on the water. I performed my own reflection at the end of the course, as they did after each exercise. What did I learn. What will I change. How will my instruction develop as a result of their experience. Here are my reflections.

From Sallie, I learned that even if someone wears hearing aids; they aren’t always going to work in windy situations. Agree on a method – a slight touch on the knee, for instance, to get their attention.
I think it’s also good to ask if anyone has any specific needs or health considerations. The previous week, I had a student with a deathly reaction to bee stings. So, we made sure she always had her epi-pen with her.
Mark demonstrated that working the room is essential. His actions reminded me that students have life experiences that translate beautifully to sailing.
Mark also brought mainstream education “accommodations” awareness into the conversation.


With Becky, I learned that even someone who has taken classes before can always expand their knowledge and gain confidence.
Also, don’t be intimidated by a person’s past experience. Keep teaching, and something will be new to them.
Gary reinforced my theory that other experiences translate well to sailing. It was so apparent that navigation skills from cycling and paddling from kayaking benefited him.
It’s worth asking students if they participate in any other activities. Yoga, cycling participation gives an idea of their physical capabilities, balance, strength, and adaptability.


From Ed I learned to watch out for the quiet ones! You might think they are not listening or engaging, but they are absorbing volumes.
This learner is likely to quietly absorb and process new information. Then they will astound you with the number of connections they make between their experiences and the instruction.
From Roy, I am reminded that most of our students will not sail solo. Most will instruct either their friends or family.
I learned it’s never a waste of my time to give students easy-to-remember mnemonics. Elementary methods may help them help their future shipmates memorize and understand sophisticated concepts.


Jim was very open about his determination playing a big role in sailing. Even someone not as young or agile as the others can take part. That’s the beauty of sailing; all ages can participate happily.
Older sailors bring a lifetime of experiences to the boat. They can helm a well-balanced sailboat with the best of them.
From Roberta, I learned that not all the sailors will go on to sail similar boats. Many students may be sailing on significantly different boats. Taking a moment to personalize methods for them is valuable.
The rest of the students also will need to adapt instruction to their ride. I like to refer to “the boat you sail most frequently” in class. The variations in reefing and heaving to boat-to-boat are worth covering.


Jon proved that even experienced sailors can learn new maneuvers. Every concept takes on a different angle with a different instructor. Honing our skills at sailing does not stop, should not stop.
Repetition of established maneuvers is valuable. The introduction of advanced concepts applied to fundamentals only makes an even better sailor.
From Tony, I am reminded that many of my students have big life experiences. Some of them are far greater than sailing a small boat. However, that doesn’t mean they walk in good at or ready for small boat sailing.
Although he formerly commanded an enormous military vessel; it was far different than sailing a smaller boat. We were able to analyze the vast difference in man overboard on a frigate versus a 16-foot boat.
You are there to teach your specialty. Your student may be famous in some other arena. That doesn’t matter. They’re there to learn from you, in your area of specialization.


From Rachel, who was my student for two weeks, I learned there is value in examining personalities. She and her husband Graham were in my class the week before, and very purposely set apart from each other.
Rachel said she likes to think through personalities, their similarities and differences, and how they will interact. I’d like to try doing more of that myself.
When a couple arrives together, the instructor may view them as a unit. However, they might not have shared experiences or motivations. Although married, they are individuals. They have different comfort levels, different levels of enthusiasm and experience, and different goals. Rachel and Graham were an example of this. Graham was reviewing, then surging ahead, while Rachel said every day was pushing her out of her comfort zone.
I will think more about this in the classes that I teach in the future. Usually, I have four students. Often it’s two couples. I will be aware that I have four individuals, not two couples, in a class.


Learning how to adjust and refine my instruction from student gains is so valuable. I was fortunate enough to have a co-instructor and a waterfront staff to assist in the sailing lessons.
My next article will cover what I learned from them, so please subscribe. That way, you get a notification when it goes live.
What I learned from each of my students the week of July 13-18, 2025.
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