Welcome to Okauchee Lake Sailing School
Since 1960, the Okauchee Lake Sailing School (OLSS) has introduced the joy of sailing to youth in Waukesha County and surrounding areas. We continue that tradition by opening our doors to sailors ages 4–18 who want to experience the fun, camaraderie, and thrill of the Okauchee sailing community.
Ages 4-12
Programs for every level from beginners to racers
40+ Years
Trusted sailing education since 1986
Full Fleet
Optis, X-Boats, and more available for students
Looking to Join?
Looking to be part of a fun, competitive sailing community? Sailing gives people of all ages a chance to challenge themselves while learning new skills from fellow crew members. Whether it’s your first day on the water or you’re a seasoned sailor, Okauchee Lake Sailing School has something for you!
Not ready to invest in your own boat yet? No problem — OLSS provides boats for new students to use, so you can experience the excitement of sailing and build confidence before taking the plunge into ownership.
Location & Directions
Okauchee Lake Sailing School
W340 N6338 Breezy Point Road
Oconomowoc, WI 53066
Entrance:
- The ground-level doors open to the Okauchee Lake Yacht Club.
- The Sailing School classrooms and lake access are located on the lakeside of the building.
Resources
OLSS Documents
2025 OLSS Calendar
Quick Links
Okauchee Lake Yacht Club (OLYC)
Inland Lake Yachting Association (ILYA)
U.S. Sailing
Racing Rules of Sailing 2021 – 2024
Getting Started
Beginning Sailing Tips
Sailing Basics: 10 Terms to Know
31 Sailing Tips for Beginners