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Sailing. That’s what we do at Go Sailing Chicago, we sail and we want to show you how. We have recruited the friendliest sailing instructors the city of Chicago has to offer. Our top-notch sailors are not only US Sailing/ASA certified instructors, they are also US Coast Guard Master Captains. You can count on our over 100 years of combined sailing experience to show you the way. We offer a variety of levels depending on your experience. There’s Sailing 101, 202, 303, and our all new Helm Time sessions.

Sailing 101 - Introduction to Chicago Sailing - Book Now

If you want to test the waters, brush up on your basic sailing skills or begin the journey of a lifetime, this is the course for you. We will show you all the basics of sailing from sail trim and shape, taking the helm and keeping a course, rules of the road, parts of the boat, proper seamanship, basic must-know knots, sailing terms, and more.

Our philosophy is that if we show you the basics on one of our boats, you will have the ability to take this knowledge and apply it to any boat on the water. After all a halyard is a halyard, a sheet is a sheet, a stanchion is a stanchion. Don’t know what these are? Don’t worry, you will as soon as you complete our sailing 101. Once you complete your Sailing 101 course, move up to Sailing 202 or try out some Helm Time.

Sailing 202 - Intermediate Sailing Lessons - Book Now

Expand your horizons by building on your basic sailing skills. Advance your knowledge of sail trim, develop a deeper understanding of how a boat moves through the water, balancing weight, keel, rudder and sails, boat handling under power, anchoring and mooring, more rules of the road, introduction to weather, and more.

You will walk away from this class with a greater sense of confidence on the water and a deeper appreciation for the elements. If you finish this class and are ready for more, take your sailing eduction to the next level and sign up for sailing 303- advanced sailing lessons or try out some Helm Time sessions.

Sailing 303 - Advanced Sailing Lessons

In this course you will be challenged with many more skills to prepare you for a lifetime in sailing. Learn to fly a spinnaker, heave to, master the man overboard drill, solidify for life the rules of the road, know every part of the boat, master your knots, emergency radio operation, and more. We will work with you in areas you want a better understanding of as well.

Upon completing sailing 303- advanced sailing lessons, you will be at a level where you can go pretty much anywhere in the world and bareboat charter a sailboat. What do we mean? Basically, you can fly to the Caribbean or the Mediterranean, charter a boat and take off for a week. You will have the sailing skills to get you where you want to go! We strongly recommend consistent practice and taking a class on navigation before attempting a bareboat charter. Consider taking some Helm Time sessions to keep your skills sharp!

Lesson Schedule

Sailing 101- Introduction to Chicago Sailing

Sailing 101 lessons are held from 9am-noon and run Saturday, Sunday, Saturday, Sunday for two consecutive weeks.

Course 1 - May 4, 5, 11, 12

Course 2 - May 18, 19, 25, 26

Course 3 - June 1, 2, 8, 9

Course 4 - June 15, 16, 22, 23

Course 5 - June 29, 30, July 6, 7

Course 6 - July 13,14, 20, 21

Course 7 - July 27, 28, August 3, 4

Course 8 - August 10, 11, 17, 18

Course 9 - August 24, 25, September 7, 8 (we skip Labor Day weekend for this course)

Course 10 - September 14, 15, 21, 22

Sailing 202 - Intermediate Sailing Lessons

Sailing 202 lessons are from 1-4pm and run Saturday, Sunday, Saturday, Sunday, for two consecutive weeks. The schedule follows the 101 courses and start on June 29th. If you have a group of 2 or more please contact us as we may be able to set up an earlier class.

Sailing 303 - Advanced Sailing Lessons

Sailing 303 lessons are scheduled as needed and will consist of 12 hours of instruction.

Helm Time ALL NEW! - Book Now

Helm Time is for students who have taken at least one sailing course or lesson and want to continue sailing in a group format. Each person will get time on the helm, trimming sails, and interacting with others with the same drive, sailing! Want more time on the water after your course? This is the option for you. Helm time is available every Sunday from 1-4pm and will be either on Mystify or Sun of a Sailor.

We welcome sailors who have taken courses with other companies to join us for Helm Time sessions.

Sailing Lessons with Go Sailing Chicago!

Class Size

We keep our sailing lesson class size to a maximum of four, with the exception of our Helm Time sessions that have a maximum of six people. If you have a group or family larger than four, and no larger than six, we will accommodate you. Minimum class size for any sailing lesson or Helm Time session is three. If we cannot fill a class with at least 3 people we will reschedule your course or Helm Time session.

Please note: No persons under the age of 18 allowed on any sailing lesson unless as part of a family group lesson. Please call, text or email us with any questions.

Our Boats

Chicago sailing lessons are taught on 3 different sailing boats ranging in size from 30-34 feet. Our varied sailing fleet is utilized to ensure we enforce the sailing skills you use on one boat can be used on another. This is what sets Go Sailing Chicago apart from the crowd.

The equipment onboard is oversized to make handling lines much easier. We meet and exceed every safety standard set out by the US Coast Guard and constantly upgrade both our gear and our knowledge. If you have any questions, a knowledgeable Go Sailing Chicago staff member is here to help.

Costs

The cost of any course is $450. all of our courses provides 12 hours of instruction. Book your course by April 1 and get $50 off your lesson (use promotion code 4113 at checkout). Sign up for two classes and receive 10% off. Sign up for all three courses and receive 20% off.

Helm Time is $100 per person, per session. Each session is from 1-4pm on Sundays starting June, 16 2013. Book 5 sessions as a package and pay only $75 per session. Book 10 sessions and pay only $50 per session. Packages can be purchased here.

Tipping is customary and and ranges from 10-20%.

Cancellations and Rescheduling

All sailing courses and Helm Time sessions must be paid in full in order to secure your spot.
If you sign up for more than one course, you will need to pay for each one in full.
Cancellations for sailing lessons and Helm Time sessions are only allowed 2 weeks in advance or more. Should you cancel less than two weeks in advance of the first scheduled class of your course or session, you will be charged the full amount of the course or session. No exceptions. For our cancellation policy click here.
You are only allowed to reschedule one time per course or session and must be done more than two weeks in advance of the first scheduled class of your course or session. Any attempt to reschedule less than two weeks in advance will be treated as a cancellation and you will be charged the full amount of the course. No exceptions.
If extreme weather conditions or major mechanical problems exist we may have to cancel and reschedule an individual class within a course or a Helm Time session. If so, we will schedule a make-up class at no cost to you.

Notices and Suggestions

You will need to come prepared for the weather the day brings. If it’s cold, windy and rainy, please come prepared.
Bring a bottle of water to keep hydrated. On hot summer days you can become dehydrated quickly.
Please come with some food in your stomach. Sailing can be hard work at times and you will need the energy to raise and trim sails.
We strongly suggest purchasing sunscreen of at least 30spf if you do not already own some.
You will need to wear non-marking, light colored soled shoes during your sailing lesson or Helm Time session. You will not be allowed to participate if you do not have the appropriate footwear. Flip flops, bare feet, and dark soled shoes of any kind are not allowed.
We provide sailing gloves and PFD’s during you lessons and sessions.
No glass of any kind is allowed during any sailing lesson or session.
Do not show up intoxicated in any way. If an instructor or any of the staff of Go Sailing Chicago suspects substance use prior to or during a sailing lesson or session you will be asked to leave. You will not receive a make up class or refund of any kind.

Please visit our faqs page for answers to more frequently asked questions about Chicago sailing lessons, Helm Time sessions, or Chicago sailboat charters.

Now let’s Go Sailing Chicago!

Book by April 1 and receive $50 Off! Use promotion code 4113 at checkout.