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 for wherever your sailing future leads, whether it is sailing the Great Lakes on Fairwind Sail Charters’ beautiful Dragon Fleet, heading south to St. Somewhere for a winter getaway, or maybe owning your own boat. You can be assured that with Fairwind Sail Charters you will get the best in sailing instruction, and our lease share program offers the best sailing value anywhere. Contact Fairwind Sail Charters now to learn about early-season specials!