top of page


Here at Windy City Sailing

Windy City Sailing started in 2004 when Captain Josef, an avid sailor and active participant in boat racing, partnered with Captain Mike. Because Chicago is such a great sailing town they quickly grew a charter boat business.  

Sharing their joy of sailing with their guests brought them something special. As they became more enamored with sailing in Chicago, they made the decision to grow their business with the purchase of the Nebula.  The Nebula is a perfect sailboat for Chicago, and Windy City Sailing guests have been enjoying sailing along the Chicago Lakefront for over a decade.

Man on deck of Chicago Sailing Charter Boat viewing sunset

Our Captains and Crew

Our Captains have 20+ years of experience sailing the Chicago Lakefront and extensive United States Coast Guard training. As a result of their extensive training they have been providing our guests with safe sailing charters for years. The Captains, crew and staff strive to provide an experience for guests that they will remember for the rest of their lives.

Captain Joe sailing
Captain Josef

Captain Josef was born and raised in Roscoe Village on the North Side of Chicago but found his love of sailing in San Francisco where he lived in the late 1990s. The first time he was onto the water he was completely taken by the pristine beauty and the feeling that sailing offered. It allowed him to truly be free and at peace. It was during these moments on the San Francisco Bay when he began learning how to sail that he became seriously interested in pursuing this hobby as a profession. Not long after he pursued his Captain’s License. Since then he has been spreading his love of sailing with others by leading exciting excursions offered at Windy City Sailing.

Captain Mike sailing the Nebula
Captain Mike

Captain Mike, a retired Chicago Fireman, has had the pleasure of sailing guests through the waters of Lake Michigan for the past twenty years.  He has been an integral part of delivering spectacular sailing charter experiences to Windy City Sailing guests from around the world.

There is something truly different for Captain Mike about being on a sailboat, as it provides an indescribable feeling. Over the years, he has continued his passion for sailing by becoming a Captain of the vessels at Windy City Sailing. He is dedicated to providing each guest with an exceptional experience.


Leave us a review on Google.    Leave us a review on Trip Advisor.

bottom of page