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 Halloween. While...

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...