Introducing our newest Dragon (with updated photos 5/22/2013): View additional photos here. read more

Fairwind is happy to contribute to this great event. We encourage everyone to come see the great art and enjoy our beautiful Village. –Capt. Ben read more

Visit Fairwind Sail Charters on Flickr to see the latest photos of the Dragon Fleet. read more

Fairwind set voyage on the social media sea this summer. Join us on Facebook to find out the latest goings on in Key Midwest. See photos and read tall tales from the Dragoneers, and keep up to date on Fairwind… read more

Fairwind, Chicago’s oldest American Sailing Association-certified sailing school, certified a record number of new ASA sailors in 2012. These new sailors now begin their sailing adventures, and it’s always nice to get their postcards from St. Somewhere! Sailing courses make… read more

Corporate America has discovered the benefits of sailing outings for their employees and clients and has found Fairwind and the magic of Key Midwest to meet their goals. Whether for team-building events or as an award for a deserving team… read more

The annual Fairwind Flotilla headed south again in February 2012. The flotilla, led by Fairwind’s Capt. Ben, sailed on beautiful yachts in the incomparable Moorings charter fleet, enjoying eighty-degree days and seventy-degree nights, fresh winds, and crystal clear waters. The… read more