PIRATES There’s something poetic about the way sailing season in Chicago ends just as Halloween arrives. The warm sunsets of July give way to crisp October wind, docks empty out one by one, and the harbor slowly transforms from a summer playground into a quiet stretch of water waiting for the big freeze. And for many of us who grew up on the lake, the end of the season wasn’t just a task on the calendar — it was a ritual. For my family, that ritual always fell just before Hal

Unlock Freedom, Confidence, and Adventure on the Water with Great Lakes Sailing When you step aboard a sailboat, you're not just learning...

Chicago, IL – Summer 2025  – The sails have come down on our very first transformative season of Sail Her Dreams , the STEM sailing...

Almost two years ago, I had a moment of quiet clarity. I was tired of being one of the only women on the race course. It wasn’t anger or...

Music has definitely shaped me into the person I am today. I wake up and sing, listen to music in the car, sing karaoke with friends and...

Sailing is like the ultimate combo of adrenaline-packed thrill  and peaceful, zen-like vibes —a little bit like riding a rollercoaster...

On the shores of Lake Michigan, as autumn leaves fall, We gather in gratitude, answering the wind’s call. The city’s skyline glows in the...

Sailing is more than just a pastime; it’s a way to connect with nature, unwind, and discover new horizons. When it comes to sailing, few...