After a wonderful summer of sailing, Fairwind Sail Charters is already looking forward to summer 2026 as we take another step closer to our Golden Anniversary in 2028. As Chicago’s oldest sailing business and premier lease share program, Fairwind thanks… read more
Thank you to the amazing Dragoneers for a great summer of sailing. With Fall in the air, it’s never too soon to start thinking about next year! Please contact us if you would like to know more about our American… read more
Spring 2024 is only a month away and sailing is not far behind! Fairwind Sail Charters offers a beautiful all-Beneteau fleet for sailing on Lake Michigan. Contact Fairwind now to learn more about Chicago’s original and still best sailing yacht… read more
Capt. Ben Sells is celebrating his 25th year as owner/operator of Fairwind Sail Charters, Chicago's oldest sailing yacht lease share program and American Sailing Association-certified sailing school. read more
As we head into the dog days of summer it is never too soon to look ahead to Summer 2022. After a year that saw record interest in the Dragon Fleet, and with a past history of having a 90%+… read more
The Dragon Fleet made up for lost time in 2020 with a great summer of sailing. Fairwind Sail Charters now looks forward to 2021 for its 43rd year of providing the best sailing experience in Chicago. With a record renewal… read more
The Dragon Fleet is up and running for its 42nd year. Given the pandemic, Fairwind is taking all necessary precautions to ensure the mighty Dragoneers have a safe sailing experience. Unfortunately, Fairwind has closed its sailing school for this summer… read more
This was a difficult season weather-wise, with most of May and June lost to rain. But it highlighted the exceptional value of Fairwind Sail Charter’s seamanship-based business model. Unlike other programs that pack their boats full, Fairwind leaves at least… read more
The buds are on the trees, the crocuses are poking their noses up, and the sandhill cranes are heading back north. Spring is here and summer is around the corner. If you have always wanted to learn to sail, let… read more