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
Fairwind Sail Charters is now accepting applications for its 2015 season. In celebration of its 37 years as Chicago’s premier sailing yacht lease share program, Fairwind is offering special pre-season pricing for sailors who sign up by November 15, 2014.… read more
Fairwind Sail Charters’ sailing yacht lease share program stands alone in offering make-up sails for sails missed due to bad weather. Fairwind Sail Charters believes that sailors should never have an economic incentive to sail in questionable or unpleasant conditions. This summer has once again confirmed… read more
Fairwind Sail Charters was honored to be part of a wonderful wedding proposal this past weekend on Chidragon. In addition to being Chicago’s premier sailing yacht lease share and sailing school, Fairwind has become quite the engagement destination. This is our seventh wedding proposal,… read more