Women in American Sailing History

By: Instructors, Sailing History, Sailing Story, women on the water

This year the whole world heard the name Cole Brauer, and celebrated the news of the 1st American Woman to circumnavigate the world. I personally wholeheartedly cheer Cole Brauer because she proves that 5’2″ women (such as myself) are powerful sailors. Go Cole!

But did you know that women have for centuries served in active roles in sailing from crew to captain? Women have been running sailing ships as far back as 231 BC having held roles as successful pirate captains and even commanding entire pirate fleets consisting of tens of thousands of pirates. The most successful pirate captain of all time wasn’t Black Beard, it was a 22 year old Chinese woman named Ching Shih. Under her leadership, the Red Flag Fleet grew to control every major Chinese pirate organization with a peak command of 1,800 ships and 80,000 pirates. For comparison, Blackbeard had only a handful of ships and hundreds of men (at best).

Today there are still women everywhere making history, and some of my personal favorites are the ones who are making history in their own ports across the world and in their own communities. So to celebrate Women’s History Month this year, I would like to celebrate some of the many women who I’ve personally witnessed making a difference in sailing.


The first among them is Mary Swift-Swan. Mary has been sailing since 1984, and in 1985 she earned her US Coast Guard license and ASA instructor certifications from 101 to 106 and has been teaching ever since. In 1997, Mary became American Sailing’s 1st Woman Master Instructor and in subsequent years was selected from amongst the 100 Master Instructors at the time to be a member of a 5-author team for American Sailing’s first two textbooks (ASA 101 and 103) as well as contributing to the ASA 110 course.

Being a woman in sailing today, I humbly thank Mary for all the many, many ways she paved the way and made sailing a place for everyone.  But Mary says,

“I don’t see myself as a ‘woman sailor’. I see myself simply as a sailor, ready to play any role aboard that needs doing.”


I asked Mary how has sailing changed for women during her sailing career and how she would like to see it change in the next 10 years, she replied:

“When I first started sailing I was surprised some men were stuck on ‘all men, manly men’ but were not as good at sailing as many of the ladies aboard. There are so many funny moments to recall. Too often when thinking of first getting into sailing, both men and women think the man should do most of the work and the lady, or youth, go along for the ride. Women don’t go for ‘the ride’ in my school. All participate.”

At Afterguard in Oakland, Mary says:

“Women are active in most aspects of sailing at my school. Women are at the front desk and on the boats. Women are welcome to participate as volunteers for the youth and introductory programs, work on boats, including to help with the engines. Afterguard is a mixed team of men and women who do not yell and who work well with all ages.”

Mary has been an American Sailing School owner since 1987 and recently celebrated 21 years at the helm of Afterguard which also has a non-profit arm; a sailing program to support the success of at-risk youth in Oakland, CA.


The next woman sailor who inspires me, is Cara Brown. I met Cara at the Annapolis Boat Show last year and immediately I was struck by her passion for sailing, her knowledge, and her ownership mentality for her role at Horizon Yacht Charters in the BVI’s. She loves her job and the joy she emanates is palpable.

At the time, I did not know that she was awarded Outstanding Instructor of the Year in 2022 (This award recognizes the top 1% of active ASA instructors worldwide), but I knew that she was someone that I wanted to have in my sailing community.

As an ASA instructor myself, I wanted to know what her favorite thing about teaching ASA courses is (aside from the obvious envious location she enjoys!).

“Seeing people go from having a sailing dream but no experience to realizing that they can learn to sail and get closer to that dream! I also love getting kids involved in sailing because then I know they might pass it onto their children one day. When I teach families, as well as making sure the parents are both competent, I always try to involve the kids and make sure they’re having a good time,” said Cara.

There is no wonder that she is a top instructor, is there? If you dream of being a sailing family, she’s your instructor down in the beautiful BVI’s!

As one of the top 1% of ASA Instructors, I also wanted to know what she would say to women sailors and to women new to sailing. To which she had another inspiring reply and said,

“I would say the same as I would tell anyone who wants to set sail – don’t wait! There is literally a whole world at your fingertips once you learn to sail,  and there are few other hobbies that can take you to so many incredible places. Sailing gives you transport, entertainment, wellness, sport and entertainment all in one and I’m constantly inspired by the places people travel to after being certified. One of my former students is currently completing the Ocean Globe Race onboard Maiden with a full female crew!”


My list would not be complete without mentioning the woman who has stewarded American Sailing since its inception 40 years ago, Cindy Shabes. Cindy is the co-founder of American Sailing and has served as the President of American Sailing since 1988, where in her role she ensures that ASA continues to be the global market leader in sailing education.

American Sailing has served over 500,000 sailors on their journey to safely, confidently, and competently pursue their sailing dreams. Whether you are a day sailor, a sailboat racer, a world navigator, or cruiser – American Sailing makes sure that sailing is for everyone.

I have the pleasure of speaking with Cindy regularly, which is incredible.

During our discussion about Women in ASA History, she shared with me what has been fundamental to the success of ASA over the past 40 years and her dreams for the next 40 years.

“Staying true to our mission, which is teaching people to sail safely and confidently, while fostering good relationships with our customers by maintaining a personal touch has been the foundation of our success.”


“My dream for ASA in the next 40 years is that we teach another 500,000 or more people to sail and that we continue to help the sailing lifestyle to thrive.”

– Cindy Shabes, President & Co-founder of American Sailing

I know that my small opportunity here to showcase amazing women in sailing does not begin to cover the many who have made, and are right now, making history. Let me know who I missed in your sailing community by sending an email to women@asa.com and let me know why they inspire you.

About The Author: Nichole fell in love with sailing at first sight in 2001 and has been sailing ever since. She eventually earned what seemed impossible, a USCG captain’s license and is certified to teach nearly every ASA certification including the new 102 which she helped lead the course development. At ASA, Nichole is responsible for Global Affiliate Development which is a perfect combination of her passion for sailing with her former career developing startup businesses as a SaaS venture capitalist. Nichole joined ASA to contribute to the avenue that made sailing possible for her and to support the 500 and growing small business entrepreneurs (affiliate schools) who make sure that anyone wanting to sail has a good teacher.

“Anyone can sail, that is if they have a good teacher”
– Nichole Ortiz, American Sailing