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.

where do i start?

At Sail Chicago, everyone starts in the same place — with an orientation. Students then progress through three course levels — Level 1: Crew, Level 2: First Mate and Level 3: Skipper Prep — at their own pace as they become comfortable with their skills.

How it works:

Prepare:

Attend a Sail Chicago Pre-sail Orientation prior to your first class and pass the US Sailing Basic Keelboat Online Course.

Learn:

Meet weekly over four weeks for each level course (12 classes total) aboard our fleet of Colgate 26 sailboats.

Checkout:

After your skipper prep class and approved checkout, pass the Sail Chicago and US Sailing online exams to become a skipper.

  • 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

    Member cost: free

  • 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.

    Cost for students: free

  • For those with basic or no sailing experience.

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

    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 students who have completed Level 1: Crew Class

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

    Student outcomes:

    • Maneuver in confined waters and gained confidence in harbor sailing

    • 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 students 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 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. Students must pass a practical on-the-water skills evaluation and a written exam at the end of the course 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.

    Student outcomes:

    • Confidently skipper a keelboat in varying conditions, exercise proper judgment, and coordinate a crew effectively

    • 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

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.

Additional classes for experienced members:

  • Sail Chicago's Performance Sailing course is taught by qualified instructors who equip skippers with the skills needed to sail safely in heavy weather and maximize their boat's performance.

    This course is designed for graduates of our Skipper Prep course or sailors with extensive keelboat experience.

    Topics include sail controls, docking, maneuvering in confined waters, rudderless steering, navigation, draft position, leech shape, reading puffs and lulls, weight balance, broaching, anchoring, sailing theory, and more.

    Classes are held on our fleet of Colgate 26 sailboats at Monroe Harbor in downtown Chicago, with a maximum of four students per boat.

    Member cost: $380

  • Prerequisite: Colgate 26 Skipper Certification

    Skippers without prior Cruising Boat experience are strongly encouraged to begin with Cruising First Mate.

    This six-lesson course teaches sailors to operate a 34-foot cruising sailboat with an inboard engine. Students 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

  • For those who have completed Basic Cruising: First Mate

    Cruising Skipper Prep is intended for those with substantial practice at the helm of a cruising boat who are ready to be evaluated in the role of Skipper

    Existing Cruising Skippers are welcome — and encouraged — to enroll in Skipper Prep for additional training. Existing Skipper privileges will not be affected for those retaking the course

    Courses include 4 scheduled classes on one of our two cruising boats, with a 5th pre-scheduled make-up class.

    Member cost: $380

  • Prerequisite: Intro to Coastal Navigation, Basic Cruising: Skipper Prep, 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 visual observations, understand 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 bearings.

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

    Member cost: $200

    No classes scheduled yet.

  • Prerequisite: Minimum two years of experience as a skipper at Sail Chicago and have run at least six Tiller Times

    Instructor Prep prepares candidates to teach at Sail Chicago. Prospective Instructor Candidates (ICs) should be competent, confident sailors with strong communication skills.

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

    Class size is limited to four students.

    Member cost: $380

Register

Tiller Times provide students with free access to boats for practice while accompanied by an experienced Sail Chicago skipper.

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 complete this online course, including all quizzes, before their first on-the-water class.

Students will receive instructions for US Sailing's online course after registering for a Sail Chicago on-the-water class.

Class Demand

Every year, demand for our classes 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 us and take their first sailing classes.

This process prioritizes returning students so they can complete our curriculum, while keeping general registration as transparent and fair as possible.

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

  • 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 or having been a member in previous seasons does not increase your odds in the lottery. However, people who were members the previous year and met the minimum service time requirement (currently 25 hours) are allowed to pre-register for classes and can skip the lottery.

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

  • No, you must sign up for the the appropriate level class based on where you are in our program.

  • Requests to retake a course will be dealt with on a case-by-case basis.

  • We do allow sailor with previous experience to skip our crew level class. First review our Instruction page to make sure you can fulfill all of the crew level requirements. Then reach out to the instruction team for an approval.

  • 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. it’s aN active community eager to learn, engage and teach.

— Frances Hartmann