Learn to Sail at Chicago in Two Locations

Our Chicago base is entering its 7th year offering ASA-certified sailing lessons to members and the general public.  Lessons are taught in two locations: Burnham Harbor in downtown Chicago and Winthrop Harbor which is located at the Illinois – Wisconsin state line.  Lessons from ASA 101 Basic Keelboat through ASA106 Advanced Coastal Cruising are offered. The sailing school is one of the few schools in the entire Midwest to offer ASA118 docking endorsement.

Sailing courses are unique at SailTime Chicago. There is no classroom work.  Students receive their study material ahead of time with instructions to arrive at lesson one prepared. Class time instead, is dedicated emtirely to on the water, hands-on learning aboard Hunter 33 foot and 36 foot yachts.

The busy Chicago sailing school employs three ASA-certified instructors, who are all highly skilled and professional teachers.  The Manager of Training Operations is Capt. Jim Stewart.  Capt. Stewart holds a 100-ton Master’s license and has been with the Chicago base since the first day.  He is beloved for his calm demeanor and the confidence he instills in all his students.

Capt. Jim Steadman has been teaching at the Chicago sailing school for 5 years and has worked primarily in Burnham Harbor.  Because of Burnham Harbor’s precarious docking situations, Capt. Steadman became certified to teach ASA118 Docking Endorsement.  It has since become one of the Chicago Members most popular classes, and has made Capt. Steadman a godsend to many new sailors.

Chicago’s newest instructor is longtime fleet manager Capt. Ryan Remsing.  At 26, Ryan is one of ASA’s youngest instructors able to teach advance level courses.  His sailing mentors?: Capt.’s Stewart, Steadman, and ST Miami’s Capt. Jim Brinckerhoff.

The Chicago sailing season begins May 1st, and lessons start immediately.  Classes are scheduled according to student demand, so please contact us for the latest schedule.

Thank you for your interest in SailTime and we look forward to serving your needs and getting you on the water with your friends and family as soon as possible! Get more info now to learn about joining SailTime in your local area. You are on the right track to an Easy, Affordable and Smart way of getting on the water!
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