How to Start a Sailing Hobby? A 20-Year Expert Shares How to Begin
Last Updated on February 26, 2025 by Boatsetter Team
For veteran sailor and Captain Jim, sailing isn’t just a skill—it’s a lifelong passion that began with a childhood experiment involving an inflatable raft, two oars, and a beach towel. Decades later, with over 20 years of experience navigating Lake Michigan, Jim has not only mastered the art of sailing but also found immense joy in teaching others. In this interview, he shares his most memorable journeys, the hidden gems of the Great Lakes, and the invaluable life lessons the water has taught him—proving that sailing is about far more than just the wind and waves.
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Tell us about the first time you went sailing
I was very young when my brother and I attempted to cross a small lake in an inflatable raft with oars. We came up with the idea to fashion a sail by tying a beach towel between the oars. To our surprise, the wind picked it up and carried us quickly to the other side. Getting back, however, was a whole different story—the wind refused to cooperate and kept blowing us backward. That little adventure sparked my fascination with harnessing the wind. It hit me after I bought my first boat. I loved everything about sailing—the freedom, the challenges, the connection to nature. But what truly surprised me was how much joy I felt teaching others. Watching someone’s confidence grow as they took the helm for the first time made me realize that sailing wasn’t just something I wanted to do—it was something I wanted to share.
What makes sailing on Lake Michigan unique?
That’s a tough one—there’s so much beauty out there. One moment that stands out was a morning after I’d spent the night on the boat. I woke just before sunrise to find three planets perfectly aligned above the water, with a faint orange glow on the horizon. The sight was surreal, as if I’d been transported to another planet. We have a saying in Chicago, if you don’t like the weather, wait 30 minutes, it will probably change! It can be calm and inviting one day, then fierce and unpredictable the next. Its freshwater is unique, and its size makes it feel like an inland ocean.
Having sailed Lake Michigan for 20 plus years, I’m sure you have so many hidden gems. But if you could share just one of your favorite boating route with us?
The crossing to Saugatuck, Michigan, is one of my all-time favorites. We usually set off in the early evening, and about six hours in, you’re far enough from shore to see the Milky Way stretching across the sky. Sometimes, you can even spot satellites gliding silently overhead—it’s truly magical. The trip takes over 12 hours, and by the end of it, you’ve experienced what it really means to be a sailor—completely reliant on your vessel and immersed in the rhythm of the water and the night sky. It’s a journey that never fails to remind me why I fell in love with sailing.
As a sailing student, what is a lasting lesson you learned that has stayed with you? And looking back, what sailing achievement are you most proud of?
Tom Barnes, a seasoned sailor from Columbia Yacht Club in Chicago, was my greatest mentor. He taught me the importance of staying cool, calm, and collected, no matter the situation. That wisdom became the foundation of the three C’s we teach all our skippers. It’s a philosophy that applies not just to sailing but to life—especially when things get wild. [On sailing achievements,] starting 3rd Coast Cruising over 20 years ago and growing it into Chicago’s largest sailing school. Helping thousands of people discover sailing and build a thriving community around it has been incredibly fulfilling.
Can you share a story about a student who particularly inspired you? And, the best part about teaching?
Over the years, I’ve been inspired by hundreds of students, but one story stands out. A woman came to us after a devastating divorce—her husband left without a word, leaving her confidence and self-esteem in shambles. She started sailing with us and kept coming back season after season. One day, she told me something I’ll never forget: ‘Sailing saved my life.’ Watching her rediscover her strength and rebuild her sense of self through sailing was incredibly moving. It’s a reminder of how powerful this experience can be—not just as a skill, but as a way to heal and grow. [The best part is] “the sailing grin”—that uncontrollable smile a student gets when the boat responds to their touch for the first time.
After all this time, how do you still find excitement in sailing?
No two days on the water are the same, and no matter how experienced you are, there’s always something new to learn. One day, you’re mastering a new maneuver; the next, you’re teaching someone else how to take the helm. Sailing challenges you to keep growing. There’s also the sense of connection—both with nature and with people. Every time I’m out on the water, I’m reminded of how small I am in the grand scheme of things. And then there’s the community—fellow sailors who share stories, skills, and a passion for adventure. That sense of camaraderie never gets old.
What’s the biggest misconception people have about the sailing lifestyle?
One misconception I often hear is that sailing is only for people with a lot of time or money. In reality, sailing is as accessible as you make it. Some of the most skilled sailors I know as crew on someone else’s boat. It’s not about owning a yacht—it’s about a love of the water and a willingness to learn. Another misconception is that sailing is relaxing all the time. While there are calm, meditative moments, sailing is often a workout for both the body and the mind. You’re constantly thinking about wind direction, boat balance, navigation, and weather. But that mental and physical engagement is part of what makes it so rewarding.
What are three pieces of advice you give to people wanting to start sailing as a hobby?
[First,] You are never too old to start learning. [Second,] sailing is something that will keep you challenged for a lifetime yet that basics are fairly easy to learn. [And last,] learn to feel comfortable with being uncomfortable. Sailing will constantly push you into situations that will challenge you. It will teach you to be adaptable to whatever the wind and water throw at you.
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This article was edited for length and clarity. Learn more about the author below.
Captain Jim is a seasoned sailor, licensed captain (Master’s 50 Ton), and dedicated sailing instructor with over 20 years of experience navigating the waters of Lake Michigan. A proud Boatsetter owner since 2017, Jim welcomes guests aboard his 32-foot Hunter Legend sailboat, offering guided sailing experiences for both seasoned mariners and beginners.
