Instruction

Sail Chicago offers an affordable way to learn to sail in Chicago. Each of our on-the-water sailing courses gives you the knowledge and skills to become a competent and confident sailor.

At Sail Chicago, everyone starts in the same place—with an orientation. From there, students progress through 3 levels of instruction at their own speed as they become comfortable with their skills.

where do i start?

Students will take three on-the-water classes before testing their skills to become a Sail Chicago skipper. The basic keelboat curriculum is divided into Level 1: Crew, Level 2: First Mate and finally Level 3: Skipper Prep.

  • A PSO gives new students and members an introduction to sailing on Lake Michigan and the workings of Sail Chicago. As a sailing cooperative with over 300 members, it is important that everyone do their part in adhering to the guidelines and maintaining the standards of Sail Chicago.

    Topics include:

    • Introduction to Sail Chicago

    • You have registered for a class on the water — now what?

    • Preparation for sailing on Lake Michigan

    • What to expect on day one of Crew Class

    • Q&A

  • All students must demonstrate knowledge of fundamental sailing skills and terminology. The best way is to take the US Sailing Basic Keelboat Online course. We encourage prospective students to learn as much as they can ahead of their course date in order to get the most out of on-the-water class. Students can request access to this course once they have registered for a Sail Chicago on the water class.

  • For those with basic or no sailing experience.

    In this course, students will convert classroom concepts into actual sailing on the water.

    At the end of this course, the student will be able to maneuver a keelboat upwind and downwind in open water using tacking and jibing maneuvers while maintaining  proper sail trim as appropriate.

    Student outcomes:

    • Recall and use sailboat and sailing terminology

    • Maneuver a sailboat upwind and downwind (tacking, jibing, recovering from being in-irons, maintaining a course, heaving to)

    • Determine apparent wind, and trim sails accordingly

    • Execute key knots

    • Communicate and coordinate with skipper and crew members

    • Recognize safety basics, club rules, and emergency procedures

    Member cost: $380

  • For those who have completed Level 1: Crew Class

    In this course students will begin to master boat handling skills and learn to control a keelboat. Topics will cover effective sail trim, harbor sailing, rescue maneuvers, departing and mooring under power and sail, using an anchor, knot tying and improved boat handling.

    After the course, students will be able to maneuver a keelboat in confined waters and will gain confidence in harbor sailing. 

    Student outcomes:

    • Plan and execute a mooring departure and mooring return

    • Get underway and return with a motor

    • Tack and jibe in confined spaces 

    • Execute close reach approaches, quick stops, and quick turns

    • Avoid collisions by knowing navigational “rules of the road” and execute emergency come-abouts

    • Evaluate and respond to heavy weather using a variety of tactics (reefing, stalling, anchoring, depowering sails, etc.)

    • Execute additional knots (heave lines, clove hitches, square knots, marlinspikes)

    Member cost: $380

  • For those that have completed Level 2: First Mate Class

    In this course, students will learn to skipper a keelboat independently with the goal of passing the on-the-water checkout and becoming a Sail Chicago skipper.

    The course is taught by qualified Sail Chicago instructors who teach advanced-level students the skills needed to safely skipper a sailboat. Students will refine their rescue maneuvers, master mooring procedures under sail and power, practice basic navigation, and learn how to respond to adverse sailing conditions. Each student must pass a practical on-the-water skills evaluation and a written exam to qualify as a Sail Chicago Skipper. This qualification is required to gain access to Sail Chicago sailboats for private use.

    Those who pass the Skipper Training course also have the option to take the US Sailing Basic Keelboat test (for an additional fee) to earn the US Sailing Basic Keelboat Certification, which includes a one-year membership in US Sailing.

    After this course, students will be able to confidently skipper a keelboat in varying conditions, exercise proper judgment, and coordinate a crew effectively.

    Read our Skipper Prep Sailing course syllabus.

    Student outcomes:

    • Think like a skipper (responsibilities and judgment)

    • Coordinate a crew

    • Recover and regroup after aborted departures and missed approaches

    • Control sail speed and determine glide zone

    • Execute a successful recovery of an overboard crew member

    Member cost: $380

Register

Additional classes for experienced members:

  • Prerequisite: Colgate 26 Skipper Certification

    This six-lesson 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, and safely maneuver our 34-foot cruising boats under auxiliary power in confined quarters.

    Member cost: $380

    Classes will be released soon.

  • Prerequisite: Intro to Coastal Navigation, Sail Chicago Basic Cruising Skipper, and Online Boating Safety course (info will be emailed to registered students)

    This course introduces the skills necessary to skipper a cruising sailboat within sight of land during daylight hours and bring it safely to anchor in a foreign port. In addition to routine equipment inspection and safety checks, participants monitor weather forecasts and conditions to choose a destination and plot a course. The crew collaborates to plan provisioning and meal preparation aboard. Underway, students use skills taught in Coastal Navigation to take hourly fixes, plot the ship's position on the chart, and calculate course adjustments as needed. The crew stays overnight in a foreign port, returning home Sunday afternoon.

    Member cost: $380

  • 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: $200

    No classes scheduled yet.

  • If you have a minimum of two years of experience as a skipper at Sail Chicago, have run at least six Tiller Times, and are interested in joining the Instructor Team, the Instructor Prep course will get you ready to teach at Sail Chicago. Instructor Candidates (ICs) should consider themselves competent and confident sailors with strong communication skills.

    The Instructor Prep program begins with a rigorous Instructor Exam based on the SC On-the-Water Skills Standards for the Colgate 26 and the Rules and Regulations. From there, Instructor Candidates shadow instructors and attend two on-the-water classes with their BKI-certified SC Instructor Trainer (SC-IT) aboard our Colgate 26 sailboats. Instructor Mentors (IMs) then observe the ICs teaching a class while conducting two Tiller Time sails. Finally, the ICs choose a mentor to guide them through their first class as a Sail Chicago Instructor.

    Class size is limited to four students per class.

    Member cost: $380

Register

All new students must complete a Sail Chicago Pre-sail Orientation (PSO) and pass the US Sailing Basic Keelboat Online Course prior to their first day on the water.

Each course meets weekly over four weeks aboard our fleet of Colgate 26 sailboats moored at Monroe Harbor in downtown Chicago. Class size is limited to four students per boat.

All students can practice what they are learning by participating in Tiller Times, which provide free access to boats while accompanied by an experienced Sail Chicago skipper.

Sail Chicago is a US Sailing-accredited program, meaning you can be confident you're learning to sail the right way — with qualified coaches and well-maintained boats.

IMPORTANT THINGS TO KNOW BEFORE YOU REGISTER.

Please read our Class Registration and Cancellation Policy before registering for any class as it addresses common questions about our courses. 

You must be a member of Sail Chicago to sign up for on the water classes. Learn more about membership and its benefits on our membership page.

The US Sailing Basic Keelboat Online course is essential to our curriculum and the best way to meet one of the prerequisites for our classes. Students with no other proof of basic sailing knowledge must take this online course, complete the quizzes, and finish before their first on-the-water class.

Students will receive instructions on how to register for the online course after registering for a Sail Chicago on the water class.

Key Dates

March 30: All courses will be published on my.sailchicago.org
April 1: Lottery registration opens
April 1: Group 1 Pre-registration begins (former First Mate students)
April 5: Group 2 Pre-registration begins (former Crew students)
April 10: Lottery registration closes 
April 14: Lottery results communicated
April 15: Group 3 registration opens
April 16: Group 4 registration opens
May 1: Remaining classes are open to the general public

Class Demand

Every year, the demand for our classes far surpasses our ability to meet it. As a result, we use a pre-registration period for returning students and a general lottery for those looking to join and take their first sailing classes with us.

This process helps prioritize returning students and allows them to complete our curriculum, and makes general registration as transparent and fair as possible.

  • For those who have recently taken a course with us, you will be offered the chance to register first for your remaining classes.

    Group 1: Those who have completed Level 2: First Mate will be given the first opportunity to register for Level 3: Skipper Prep classes.

    Group 2: Those who have completed Level 1: Crew can register for Level 2: First Mate and the Level 3: Skipper Prep classes.

  • Every year, the demand for our courses is far beyond our ability to meet it. For reference, last year we had approximately 80 Crew seats available across 20 courses. By the end of the season, there were nearly 450 people on our waiting list.

    General Lottery Registration will open April 1. The lottery will stay open for 10 days and closes at 11:59:59 pm on April 10. On April 14, the lottery will be drawn and preople who signed up for the lottery will be sorted into groups of 10. You will be contacted at the e-mail you registered with and it will contain your group number and registration date.

    On April 15, Group 3 (the first lottery group) will have the opportunity to register for any open classes. 24 Hours later, the next Group will be granted access to register. This will continue group by group until all classes are filled.

    On May 1 - all remaining classes will be open for registration without restriction.

Lottery sign-up

Frequently asked questions

Please review the most commonly asked questions regarding class registration before contacting us.

  • No. Having a membership does not increase your odds nor does having been a member in previous seasons.

  • No. You can register any time after registration opens up for your group.

  • Please see our Class Registration and Cancellation Policy under the heading “Selecting the Appropriate Course”

  • Requests to retake a course will be dealt with on a case-by-case basis. Similar to last season, there will be a form (to be linked once it’s created) for these requests.

  • If you have not taken a class with us before, you will need to go through the General Lottery or wait until classes have opened to everyone. Last season there were still a handful of seats left in the Skipper Prep classes.

  • Unfortunately, that’s the way things go sometimes. Our lottery grants the chance to Register for a course, not for the course itself.

  • With the way the lottery runs, we can’t guarantee you’ll be able to get into the same session.

  • This plan only pertains to our Learn-To-Sail Curriculum (Crew, First Mate, Skipper Prep). Cruising courses will be announced and rolled out separately.

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“

sail chicago is more than sailing. its a community with members from all over the city.

-Alejandro Jimenez