Summer Romance Blooms on Dragon Fleet!

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

Location, Location, Location

What is true of your home on land is true of your home on water.  Fairwind Sail Charters has the best location in Chicago sailing.  In Burnham Park Harbor, at the heart of the Museum Campus, right across the street… read more

Dragon Fleet Hits the High Seas!

Fairwind Sail Charters kicked off the 2014 season in style.  Beautiful day, beautiful boats, and of course beautiful people!  Fairwind’s lease share program is the oldest (and best) in Chicago.  Founded in 1978, Fairwind Sail Charters is also the oldest… read more

Celebrate Spring in Key Midwest!

Our first 70+ degree day here in Key Midwest this season!  Definitely time to shake off the winter doldrums and start gearing up for sailing season.  Whether you are a new sailor looking for sailing lessons or an Old Salt… read more

Fairwind Offers Free Summer Specials!

Fairwind Sail Charters, Chicago’s premier sailing lease share program, is offering Free Summer Specials on both its 40 and 37 foot Beneteau sailing yachts!  Sign up before April 30, 2014, and receive an additional sail at no extra cost!  Need sailing lessons?  Fairwind Sail Charters is… read more

Make this a Fairwind Summer!

As the snow melts and the days grow longer, now is the time to get moving on your summer plans. Fairwind Sail Charter’s sailing school, Chicago’s oldest American Sailing Association certified sailing school, just had the pleasure of having an… read more

Fairwind Springs Ahead!

With Spring around the corner, Fairwind Sail Charters is preparing for a great sailing season!  Fairwind’s ASA-certified sailing school is signing up students for sailing lessons on its fleet of beautiful Beneteau yachts and is also welcoming new skippers to… read more

Fairwind Now Accepting Applications for 2014

After a banner year, Fairwind Sail Charters is signing up students and lease share skippers for Summer 2014. “Our American Sailing Association certified sailing school, the oldest in Chicago, certified a record number of students this season,” said Capt. Ben… read more

Fairwind Sail Charters Supports Riverside Juniors

RJWC is bringing back the tasting sensation: Pizza Fest!  Mark your calendars and prepare to enjoy pizza from the many restaurants around the community.  The event will be held on Saturday, September 28th from 6:00 – 10:00 PM at the… read more