Sail Chicago is the most affordable way to learn to sail in Chicago. Each of our 4-week, on-the-water sailing courses gives you sailing knowledge and skill, and puts you on the road to being a confident skipper. 


 
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Sail Chicago is a US Sailing accredited sailing school, which means you can be sure that you're learning to sail the right way, with qualified sailing coaches and well-maintained boats. 


PRE-SAIL ORIENTATION

This class gives you an introduction to the sport of sailing and Sail Chicago. You'll learn how to prepare before going sailing, brush up on sailing terminology, equipment, safety rules and emergency procedures, and ask questions before the Sail Chicago season begins. First-time students who've enrolled in our classes will receive US Sailing handbooks and handouts, and an orientation.

Free (and REQUIRED for new Sail Chicago members and students)


BASIC

If you’ve just become interested in sailing, our Basic program is for you. Basic students will learn the fundamentals of sailing on the water with a certified Sail Chicago instructor. The course teaches sailing principles, boating safety, crew work and beginning sailing maneuvers. If you're a Sail Chicago member, you can practice what you’re learning with access to our Tiller Times, which give free access to boats while being accompanied by experienced Sail Chicago skippers. 

Classes are conducted on our fleet of Colgate 26 sailboats and are held at Chicago’s Monroe Harbor in downtown Chicago. Class size is limited to four (4) students per boat. 

Member cost: $240

Non-member cost: $315 (no access to Tiller Time)


INTERMEDIATE

If you’ve sailed before, but want to further hone your skills as a skipper, Sail Chicago’s Intermediate program is for you. Students will learn effective sail trim, harbor sailing, man-overboard drills, using an anchor and fine-tuning your boat handling on the water with a certified Sail Chicago instructor. Practice what you’re learning with access to our Tiller Times, where Sail Chicago members can sail and practice techniques for free, accompanied by experienced Sail Chicago members. 

Member cost: $240

Non-member cost: $315 (no access to Tiller Time)


ADVANCED / SKIPPER PREP

Sail Chicago’s Skipper Prep course will teach advanced-level students everything they need to know to skipper a sailboat. Students will learn rescue maneuvers, docking and mooring procedures under sail and under power, important knots, simple navigation, boat tuning and how to get out of bad sailing conditions. Passing this course and a skills evaluation grants members access to Sail Chicago sailboats for private use. In addition, you will qualify to take the examination for US Sailing Basic Keelboat certification.

Classes are conducted on our fleet of Colgate 26 sailboats and are held at Chicago’s Monroe Harbor in downtown Chicago. Class size is limited to four (4) students per boat.

Those who pass our Skipper Training course can take the U.S. Sailing Basic Keelboat test and pay a fee in order to gain U.S. Sailing Basic Keelboat Certification which includes a 1-year membership in U.S. Sailing.  

 

Member cost: $240

Non-member cost: $315 (No access to Tiller Time) 


Coastal Navigation

Coastal Navigation teaches sailors to identify chart symbols and their corresponding visual observations, define true and magnetic compass readings, determine deviation and variation, plot course and position, calculate time/speed/distance, take bearings and fixes; adjust for set and drift; and plot danger fixes.

Students complete navigational exercises with charts, dividers and parallel rulers. Aids to navigation and rules of the road are covered in a pre-class assignment online.

Member cost: $125

Not available to non-members


Basic Cruising

This course teaches sailors to operate a 34-foot cruising sailboat with an inboard engine. Enrollees learn to apply their skipper techniques to a larger boat, use enhanced safety features, operate and maintain the engine and electrical systems, navigate, and safely dock the boat.

Prerequisite: Colgate 26 Skipper Certification

Member cost: $240

Not available to non-members


Bareboat Cruising

This course teaches the skills necessary to skipper a cruising sailboat within sight of land and bring it safely to anchor in a foreign port. Students will learn to check safety equipment, perform daily engine and mechanical checks, check water holding systems, use a hand bearing and ship's compass, estimate their position, and maintain a course with time/speed/distance calculations. Students will also learn how to use GPS systems for  navigation.

This weekend course starts on a Friday afternoon and ends on Sunday. The boat will spend the night at a foreign port and return to Chicago the next day.  

Prerequisite: Coastal Navigation, Basic Cruising

Member cost: $240

(Special 5-day bareboat class: $300)

Not available to non-members


Rhodes Spinnaker

Learn to set and fly a small spinnaker on one of our Rhodes 19 sailboats. You'll learn about to to prepare, set and keep a spinnaker sail flying in varying conditions. 

Prerequisite: Intermediate Sailing, or Colgate or Rhodes Skipper certification

Member cost: $100

Not available to non-members