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Welcome to OLSS! Registration for all 2024 classes is OPEN!

Okauchee Lake Sailing School registration opened on January 1. Click here to register.   


As you explore the site and registration please contact the Webmaster with any issues, comments or concerns.  

Click here for the Official 2024 Calendar

Click here for the summer 2024 calendar for all classes & regattas

Click Here for Summer 2024 Registration

Click here for registration link

Okauchee Lake Sailing School

For 57 years the Okauchee Lake Sailing School has been introducing sailing to youth in Waukesha County and surrounding areas.  The tradition will go on in 2024 as we will open our doors to kids ages 4-18 who want to experience the fun, camaraderie and thrill that the Okauchee sailing community has to offer.  The OLSS will provide opportunities for beginners who would like to learn how to sail, intermediate sailors who wish to continue honing their skills and advanced racers who are ready to measure their skills against the top competitors from other Inland Lakes.

Contact Us

Okauchee Lake Sailing School

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Looking to Join?

Looking to be a part of a fun, competitive sailing community? Sailing gives people of all ages a chance to challenge themselves while learning skills from other crew members. Whether it is your first day on the water or you are a seasoned vet, Okauchee Lake has something for you!

Getting Started?

Interested in sailing but not sure where to start? Look no further! Set your sails toward these new to sailing articles we have compiled just for you. They will walk you through some tips to be a successful sailor. 

Beginner Sailing Tips

Sailing Basics: 10 Terms to Know

31 Sailings Tips for Beginners

Find Us

Okauchee Lake Sailing School  

Street Address: 

W340 N6388 Breezy Point Rd

Oconomowoc, WI 53066


Mailing Address:

Okauchee Lake Sailing School, Inc

P.O. Box 152

Nashotah, WI 53058