Fairwind Sail Charters

A beautiful day in Chicago always makes these sparkle a little brighter ✨ Meet our Dragon Fleet, featuring four beautiful Beneteau yachts.

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 as we take another step closer to our Golden Anniversary in 2028. Fairwind is Chicago’s oldest sailing business and offers the best sailing program anywhere. Beautiful boats and exceptional customer service is the Fairwind Difference. Isn’t it time for you to join the Fairwind sailing family? Sign up before April 15 and get a free additional sail on us!

Spring into sailing for summer 2026 and get a free additional sail! – Fairwind Sail Charters, Inc. Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 a

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 as we take another step closer to our Golden Anniversary in 2028. Fairwind is Chicago’s oldest sailing business and offers the best sailing program anywhere. Beautiful boats and exceptional customer service is the Fairwind Difference. Isn’t it time for you to join the Fairwind sailing family? Sign up before April 15 and get a free additional sail on us!

Spring into Sailing for Summer 2026 and get a free sail! – Fairwind Sail Charters, Inc. Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 a

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 the mighty Dragoneers for their friendship and support over the years. Isn’t it time for you to join the Fairwind sailing family? Our lease share program is unlike any other. Contact us now to learn about the Fairwind Difference that always puts your safety first.

Fairwind Sail Charters Now Accepting Applications for Summer 2026 – Fairwind Sail Charters, Inc. 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 i

As we enter the dog days of summer, it is worth emphasizing the value of Fairwind Sail Charters business model that is based on seamanship. Fairwind Sail Charters is the only lease share program that provides makeup sails for sails missed due to bad weather. Fairwind provided makeup sails earlier this summer when Chicago had excessive heat, and even for several days when there was practically no wind. Fairwind never wants to put a financial pressure on a skipper to sail in poor or questionable conditions. Fairwind schedules its boats so there is plenty of open time to supply safe, pleasurable sailing for its dear Dragoneers. That's just one more example of the Fairwind Difference:

The Fairwind Difference – Fairwind Sail Charters, Inc. Sailing is Fairwind's full-time business, not a freelance sideline, and its customer service is unequaled. Over 90% of Fairwind skippers are repeat customers, m

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 Sailing Association certified sailing school or our premier sailing yacht lease share program. Come sail with us and experience the Fairwind Difference!

Fairwind Sail Charters Now Accepting Applications for Summer 2025 – Fairwind Sail Charters, Inc. 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 u