Learn to Sail Here and Sail


Scroll down to see all of your options or to get a good look at the background picture. If you have a coupon, you may enter it now (best) or at checkout.

A) Click on the type of Lesson you want. The calender pops up with the first available date for that Lesson Notice that the first day of the week is Monday, importantly, this puts the weekend, Friday, Saturday & Sunday at the end of the same line.
B) While on the Calendar, You may click on the Sail you picked or the edit icon on the right to go back and pick a different type of Sail.
C) If you and one or more friends are sailing together, change the quantity now to the number of spots you want. You always can schedule qty 1 multiple times if you prefer.
D) Change the month if you need and pick a date & time that you want to sail. If this is the correct date & time and there are enough spots open, Click on Add This Date & Go to Check Out. If you want this date and another date (multiple lessons as an example) Click on Add This Date & Then Add Another. If you want a different date or time, just click on the different date.
E) When you are finished (all the dates you picked are listed at the bottom of the page) go to checkout. At check out, all the dates you picked are at the top of the page above where your name is entered and above the change button. Click on change if you want to go back and change your schedule. Otherwise, if everything is correct, fill in your Name and other information, digitally accept and sign the waiver, and click on Pay Now at the bottom.
F) Click Log In to pay with your paypal account or Click Pay With Debit or Credit Card to pay with any debt/credit card. Complete the payment and you are done. Sit back and enjoy that you are starting a Lifetime Adventure.
G) Looking forward to seeing you on the water soon!

Click To/For




   You May Scroll or PageDown to See the Whole Background Picture!

Scheduling Page Updated/Verified 3/18 


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