This year marks Fairwind Sail Charters’ 40th anniversary and my 20th anniversary as owner When I bought Fairwind in 1998 I started what has now been a twenty-year experiment. Could you run a sailing business based on the principles of… read more
The newest addition to Fairwind Sail Charters’ legendary Dragon Fleet has left its nest in Marion, South Carolina, (dragons start out in nests) and is headed to its new home on Lake Michigan. To be christened Dragonfly, it is a… read more
Capt. Ben Sells’s latest book, The Tunnel Under the Lake: The Engineering Marvel that Saved Chicago, is featured in the Northwestern University Press 2017 Spring/Summer catalog and was chosen as the lead book in the new series “Second to None:… read more
Fairwind Sail Charters celebrates its upcoming 39th year with Special Fall Pricing on a brand new 2017 Beneteau 38.1. The Beneteau 38.1 combines practical features, performance, and elegance on a beautiful yacht that epitomizes the cutting edge for family cruising.… read more
Get a head start on your sailing future with Fairwind Sail Charters, Chicago’s oldest American Sailing Association-certified sailing school and the number one choice for cruising sailors for almost forty years. Learn to sail with the best and be ready… read more
Fairwind Sail Charters welcomes a new addition to the best sailboat fleet in Chicago. The 2016 Beneteau 41 is designed by naval architects Finot-Conq and Associates. It features a sleek low profile cabin with long coachroof windows and a continuous chine over… read more
With the exception of a cool and rainy start, summer 2015 has provided picture-perfect sailing. It was a season that saw a record number of students graduate from Fairwind’s award-winning American Sailing Association sailing school, many happy skippers enjoying the beautiful… read more
Fairwind Sail Charters always puts safety first, which is why it is the only sailing lease share program to offer makeup sails to skippers who miss a sail due to bad weather. “I never want a skipper to feel financial pressure… read more
Get a head start on your sailing future with Fairwind Sail Charters. Chicago’s oldest American Sailing Association certified sailing school and the number one choice for cruising sailors for almost forty years. Learn to sail with the best and be… read more