Learn to Sail Here and Sail

       Practical Sailing Lessons

We have 3-hour Sailing Lessons

Every Morning from 9 am to 12 noon,
Every Afternoon from 1 to 4 pm, and
Every Weekday Evening from 6 to 9 pm or Every Weekend Evening from 5 to 8 pm.

All of your lessons are taught by a US SAILING certified instructor on a 35' sailboat with an inboard diesel engine, marine radio, weather/chartplotter, running lights, and bathroom among (many) other things.

We think these are the basics but no other sailing school in Chicagoland can boast that!

This is a practical on-the-water lesson. As you progress through the curriculum, you will participate in every aspect of sailing a boat. You will start by learning to rig the boat and you will take the helm in the first lesson.

       Advanced Spinnaker Lessons

Our Advanced Spinnaker Lessons are every Sunday for 3.5 hours. We take a maximun of 4 students and you learn the ins and outs of spinnaker sets, handling, trimming, gybing, peeling, and dousing with our normal crew.

This is advanced stuff and it takes a lot of knowledge, teamwork and practice.

Click 'Spinnaker' button to Schedule Your Lesson:       Spinnaker

       Wednesday Night Racing Lessons

If you want to be part of a winning crew, become a team player. Keelboat racing is a team sport. As in any team sport, there is individual accountability but in no other sport is there more team play. Many evolutions on a sailboat need individual teammates to execute their maneuvers in precise order and synchronization. It takes knowledge and practice. You must be prepared and this class is how you get prepared.

We take a maximum of two students on Wednesdays.      Racing  

You will learn, hands on, on the water and you will partake in an actual sanctioned sailboat race experiencing firsthand the thrill, camaraderie, team work, individual accomplishment, competitiveness, strategy and beauty of sailboat racing. You are not going to take a class and then simulate a sailboat race; you are going racing!
For many, this can be an experience of a lifetime. For some, the lucky, this will become a way of life.

       Private Lessons

If you would like private lessons on our boats or yours, please contact us directly (Click Here) to schedule.

Rick's Quote

"Learn to Sail Here and
    You Can Sail Anywhere!"

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Lessons Page Updated/Verified 2/18 


Had a great time sailing. Great way to spend a Saturday in Chicago.

  -Kat K, November, 2017

Rick was an amazing teacher. Very knowledgeable and accommodating for however involved you wanted to be. I wanted to be very hands on and he let me work on a ton of different aspects and was helpful throughout. We went through some good weather and some not-so-good weather on my 5 sails, but they were all amazing. Would recommend!

  -Phillip E, October, 2017

Rick was on time and gave a good introduction to what we'd be doing. He was very accommodating to the 4 of us and really fun to talk to. We thought 3 hours might be too long but it went in the blink of an eye. Learned a lot about Chicago and boating in general. We will do it again next time!

  -Elise M, October, 2017

MY husband and I had a wonderful time on Sailboat-Lessons.com. We highly recommend it!

  -Mary J, October, 2017

I've sailed with them a couple times this past summer. Captain and crew are great! They do a great job of teaching you, while still having a fun time out on the water. Looking forward to some more lessons this summer!

  -Claire K, February, 2017

The captain was super awesome and very good about letting you know what all is happening with the sailboat! This was the high point of our Chicago trip!

  -AJ, October, 2016