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About  Captain Lynda Stephens

"Bringing my passion for sailing to women that might otherwise not have the opportunity or might feel intimidated by all there is to know is my here and now work. Learning, love, and connection are the rewards I never dreamed would be so rich, so beautiful."


Ahoy! I’m Captain Lynda, the owner of The Joy of Sailing. Thanks for checking out The Joy of Sailing Women’s Sailing Club. For those curious about my background and experience, here’s a bit of my story.


I was raised in Connecticut sailing with my family. After high school I moved to California where I sailed the Pacific with my dear friend Steve. I married, was divorced after 25 years, and moved my life to Chicago in 2013. Here I returned to my love of sailing and my buddy Rick Stage blessed me with an opportunity to sail with his crew in the Race to Mackinaw 2014. Amy Strittmeyer was our captain and an inspiration to me. 


In 2015 I got my captain’s license after attending US Maritime Academy Chicago. I had been crewing for my friend Jeff for a couple years and then together we purchased Vagabond; a beautiful 40’ sloop. We took hundreds of people on charters over the course of several years.

In 2018 I purchased Sea Biscuit. A rigid bottom inflatable power boat. She was a great “dinghy” for Vagabond and later became the pilot boat for The Preservation Pirates a citizen-based harbor clean up non-profit organization with the motto “Debris is our Booty!”.


Although being a charter captain was fun, in 2019 I felt called to do more with my experience and abilities and started a women’s sailing program. With the help of my friend Jeff, I found Leela (Sanskrit for “creative play by the divine”). She’s a 30’ Catalina much more suitable for learning how to sail. And the beat goes on.


  • OUPV & 50 Ton Master Captains License with Sailing and Towing endorsements

  • Certified US Sailing Keelboat Instructor

  • Minister Universal Church (for conducting nautical weddings)

  • First Aid/CPR

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