Sailing instruction begins with a Pre-Sail Orientation held on dry land in a classroom. All new sailors are required to attend whether you have signed up for the Sail into Summer option or enrolled through the New Member Package. One 2-1/2 hour class provides an orientation to this great sport and introduces you to Sail Chicago and our activities.

The class briefly covers parts of a sailboat, sail theory, terminology, sailing gear, knots, and boating safety. You will learn what you will need to be prepared for your first on-the-water class. You will receive a textbook and handouts and information on your on-the-water class. This is also a great opportunity to meet other sailors and find out about sailing-related activities for the entire summer.

Class Dates:

• Saturday, April 28 @ 10:30 AM – 12:30 PM
• Tuesday, April 17, May 22, June 26, July 24 @ 6:30 PM – 8:45 PM

Class Location:
Lincoln Park REI Store
1466 North Halsted Street
Chicago, IL 60642
(312) 951-6020
Get Directions

Basic Sailing is designed to provide an enjoyable introduction to the sport of sailing, designed for people new to sailing as well as those who have ridden on a sailboat but have not had much time steering the boat.   You can enjoy Chicago’s beautiful lakefront from the water and embark on a lifetime adventure!

This is a hands-on class—you will be sailing the boat in your first lesson!  Over the course of four, 4-hour lessons, you will learn to read the wind, rig the boat, get underway, set your sails, maneuver the boat upwind and downwind, tack and jibe, and return to the mooring.  You will learn the fundamentals of sailing theory, safety on the water, boating “rules of the road”, sailing knots, and weather. 

Basic Sailing classes are held on our Colgate 26 at Monroe Harbor in downtown Chicago, with a maximum class size of four students.  Classes meet once per week for four weeks or twice per week for two weeks.

Cost: $250 for Sail into Summer option; included with New Member Package
Prerequisite: Pre-Sail Orientation class
Questions? Email instruction@sailchicago.org

Intermediate Sailing is the follow-up to Basic Sailing and is also designed for sailors who have some experience at the helm of a small to medium sized keelboat.  This course prepares you to skipper a sailboat boat under the guidance of an instructor or experienced sailor, both on Lake Michigan and in busy Monroe Harbor.

This course is designed to develop your boat handling skills, harbor sailing, and crew management abilities. You will review basic sailing skills and expand your knowledge of points of sail, sail trim, weather, and right-of-way rules.   You will learn close-quarters boat handling, reducing sail (reefing), anchoring, crew overboard recovery and safety/emergency/rescue techniques.

If you are taking Basic Sailing as a new member and want to enhance your skills this summer, you may add Intermediate sailing in a subsequent session.  This course is an important part of the process of obtaining your Sail Chicago Basic Keelboat Qualification and is a prerequisite to enrolling in the Skipper Training class.

Intermediate Sailing classes are held on our Rhodes 19s with a maximum class size of three students.  Classes meet once per week for four weeks or twice per week for two weeks. 

Cost: $200
Prerequisites: Membership, Pre-Sail Orientation, and Basic Sailing or Previous Sailing Experience 
New members: this course can be substituted for Basic Sailing as part of the New Member Package if you can demonstrate sufficient experience sailing a small keelboat. Please indicate your experience on the registration form.
Questions? Email instruction@sailchicago.org

Skipper Training provides sailors with an opportunity to solidify material learned in Basic and Intermediate Sailing courses. The purpose of the course is to develop the additional skills required to skipper a boat on your own. New members who have sailed a boat on their own may enroll in this course as part of their New Member Package.  Successful completion of this course is required in order to qualify to reserve and sail our boats on your own.

This course enhances your small boat handling skills, including harbor sailing, mooring departures and returns under sail, crew overboard recovery, crew coordination, and heavy weather sailing tactics. You will review weather, safety on the water, and Sail Chicago procedures.

Skipper skills will be evaluated throughout the four‐lesson course. Completion of the course with demonstration of adequate mastery of the required skipper skills may satisfy the on‐the‐water portion of the basic keelboat checkout requirements, subject to Instructor recommendation. Your on‐the‐water evaluation is integrated into the Skipper Prep Course.

Skipper Training classes are held on our small keelboats (Rhodes 19 and Ideal 18) in busy Monroe Harbor with a maximum class size of three students.  Classes meet once per week for four weeks or twice per week for two weeks.

Cost: $200. 
Prerequisites: Membership, Pre-Sail Orientation, Intermediate Sailing. 
New members: this course can be substituted for Basic Sailing as part of the New Member Package if you can demonstrate sufficient experience skippering a small keelboat. Please indicate your experience on the registration form.
Questions? Email instruction@sailchicago.org