Chicago

Sailing School

Learn to Sail With SailTime!

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Unparalleled Excellence

SailTime University

SailTime Chicago conducts ASA-certified sailing lessons in downtown Chicago and Winthrop Harbor, IL. Chicago’s Burnham Harbor provides a premier location for our downtown sailing lesson operations. It offers wonderful facilities and is easy to reach by bike, train, or car. North Point Marina in Winthrop Harbor is the largest marina on the Great Lakes and offers world-class facilities. The marina is located in the Illinois Beach State Park and is easily reached by the Metra North Line.

Our Training Philosophy

Our approach to sailing lessons is different than most. Class size is restricted, and we train on cruising class boats; not on small, open-deck day sailors. If your dream is to sail a large boat, we believe you should learn on a large boat. Since all our boats are equipped with roller-furling jibs and mainsails, students will be trained on the modern rigs that are becoming common in the larger charter fleets around the world.

Our typical training day starts at 9:30 am and goes until 5:30 pm. It is completely hands-on work; no time is spent on classroom work except for a test at the end. Unlike most other schools, we spend class time teaching how to handle the boat under power in and around the harbor and slips.

Accelerate Skills Development

Experiential Education

We do not have a “one size fits all” approach to learning. Give us a call and let’s work together to design the correct class structure based on your schedule, experience, and educational needs and abilities. Specialty classes for events like corporate team-building can also be designed.

Combination Courses

It often makes sense for students to combine 2 or more ASA certifications into one extended class. We can save experienced sailors time and money by allowing you to “test-out” of lower certification levels. Or for those with limited time away from work, you can earn multiple certifications into a shorter period of time. Here are some of our most popular combinations:

ASA 101/103:
A 3-day, 2-night course covering the material of ASA 101 Basic Keelboat and ASA 103 Basic Coastal Cruising. Recommended for experienced day-sailors who are interested in cruising, but need the 101 certification first. $900/student *CALL TO BOOK*

ASA 103/104:
A 3-day, 3-night course covering the material of ASA 103 Basic Coastal Cruising and ASA 104 Bareboat Charter. The course is built like a short charter vacation and is great for families or couples interested in chartering in the Caribbean. $1,150/student *CALL TO BOOK*

All of our instructor-captains are USCG-licensed and ASA-certified.
SailTime supports the national recreational boating education standards as recognized by the United States Coast Guard.

ASA 101 Course

This is a 2-day, hands-on course covering the basics of sailing and boat handling on a 30’+ sized sailboat. Max of 4 students per class.

ASA 103 Course

Students will learn the skills to perform as skipper and crew of a 25-35 foot boat by sailing in coastal waters.

ASA 104 Course

This course is structured along the lines of an actual charter: students will learn during a 2-day live-aboard cruise.

ASA 105 Course

The ASA Coastal Navigation Course (ASA 105) is a two-day (16 hour) classroom course with SailTime’s Capt. Jim Johnson.

ASA 106 Course

Students will learn how to safely act as skipper and crew of a sailboat 30 to 50 feet in length in near coastal and inland waters.

ASA 118 Course

This 1-day course is designed to teach docking in high wind situations, covering theory and techniques to dock and undock boats in an efficient manner.

ASA 101/103 Combo Course

A 3-day, 2-night course covering the material of ASA 101 Basic Keelboat and ASA 103 Basic Coastal Cruising.

ASA 103/104 Combo Course

The ASA 103/104 course is a 3-day, 2-night course covering the material of ASA 103 Basic Coastal Cruising and ASA 104 Bareboat Charter. 
Learn to Sail

Boating Education

SailTime supports the national recreational boating education standards as recognized by the United States Coast Guard.