Women Sailing Instructors

Women Teaching Sailing

Confidence, Connection, and Change
Picture of Jenny
Jenny
Women Sailing Instructors

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By Jenny McCain, Director of Educational Development
Estimated reading time: 7 minutes

It’s the hesitant question that so many women ask when they call to register for a sailing course, often apologetically: “And… do you have any lady instructors?”

We know why the question comes up. Too many have had discouraging experiences with captains whose swagger or bark was more than a new student wanted to handle. No one should ever be bullied or belittled on a boat. Sometimes it’s not even outright harshness, but the subtle, “Let’s give that harder task to someone else,” that can hurt just as much.

Women on the water
Women on the water

Of course, in an ideal world, gender wouldn’t matter. Good instructors, no matter the gender, should be patient, kind, and skilled at helping new sailors gain confidence. Yet some instructors never quite learn how to support a timid or hesitant student, or how to draw out the person who’s shy about asking questions. There isn’t a formal teaching academy for captains, after all; most of us learned by mentoring under more senior instructors.

This isn’t a rant against male instructors because most are excellent. And in my own experience as a captain and instructor, I’ve had countless crews of men who were eager learners and just as respectful of me as a female captain. On the first day of an ASA-101 course, when I mention that I taught kindergarten for four years, I usually hear a chorus of men saying, “Perfect! Then you’ll know how to teach me!”

Women on the water

Still, the need is clear: we need more women to step into this career. If you’re a woman who loves sailing, maybe it’s time to consider teaching. Do you already have a strong sailing résumé? That’s a great place to start. When I began, I had years of small-boat sailing and teaching under my belt, but moving into larger boats required mentorship. I spent time with boat repair technicians while I studied for my captain’s license, and those guys taught me about engines, batteries, changing electrical switches, splicing lines, even how to stain teak decks. They don’t like to brag that they helped me get my start on big boats, so I still go down to the marina and do the bragging for them in front of their students.

The rewards of teaching are many. The flexible schedule is appealing. Being a female captain also offers an immediate connection for other female students who feel hesitant; they see you as someone who can help them rather than intimidate them. And perhaps best of all, you meet extraordinary people. I’ve had students from every continent except Antarctica, each bringing their own stories (wow, the stories!) and excitement to the boat.

Instructor Jenny McCain

The path forward is pretty clear. Start by determining which captain’s license your experience qualifies you for. Then connect with an ASA school that will let you mentor under an instructor, and when you’re ready, reach out to ASA about attending an IQC (Instructor Qualifying Clinic) to become certified. Like any career worth doing, it takes some effort, but the rewards are incredible. The first time a student you only knew for a few days texts you later to say thank you for launching them on a lifelong sailing journey, you’ll realize just how much of a difference you can make.

NorthU Women's Performance Race Week
NorthU Women’s Performance Race Week

So here’s my plea: ladies, if you love sailing and you have the skills, consider becoming an instructor. The industry needs you, the students need you, and the water is waiting.

About the Author

Jenny McCain is an ASA instructor and the Director of Educational Development at American Sailing. She has dedicated her career to improving sailing education and supporting instructors worldwide. For questions about becoming an instructor, email her at jmccain@americansailing.com.

Jenny McCain ASA Sailing Instructor
  • Women Teaching Sailing

    Women Teaching Sailing


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    Ready, Set, …Instruct?



Join The Discussion

  • Women Teaching Sailing: Confidence, Connection, Change, and Inspiring Leadership

    Posted by American Sailing on September 26, 2025 at 6:52 pm

    Jenny McCain describes both the challenges and the unique value women bring as sailing instructors. How might increasing the number of female captains and instructors change the culture of sailing education, and what barriers do you think still exist for women entering this role?

    Check out Jenny’s article here: https://americansailing.com/articles/women-teaching-sailing/

    American Sailing replied 1 hour, 59 minutes ago 1 Member · 0 Replies
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