Adult Sailing School – Oakville Yacht Squadron

Registration now open

Adult Sailing Programs

The OYS Sailing School follows the CANSail Learn to Sail program. Whether you are looking to try something new, learn to sail or want to buy a boat in the future, this is the place to start.

The OYS Sailing School Adult program provides a safe and enjoyable introduction to sailing and boating on a dinghy or keeplboat as well as an advanced dinghy course. Our programs are designed for all learning objectives and levels of experience. Our adult program offers small classes sizes.

Intro dinghy

No prerequisites required
Individuals 16+ years old

The OYS Sailing School follows the CANSail Learn to Sail Program. Whether you are looking to try something new, learn to sail, or want to buy a boat in the future, this is the place to start. Adult programs are taught in our dinghy class of RS Quests, accommodating up to 3 adults in each boat. This program provides a safe and enjoyable introduction to sailing and boating. The program is designed to teach the basics of dinghy sailing at CANSail level 1 including boat balance, sail trim, heading up, tacking, gybing, leadership, knots, basic weather patterns, docking and sailing terminology. These skills are taught through unique lessons by our team of qualified and experienced instructors. CANSail certificates are awarded upon successful completion of a set of practical skills and demonstrated knowledge.

This course is taught on Monday and Wednesday evenings in 2025 from 5pm – 8:30pm over 2 weeks; for 14 hours of sailing!

Session 1: June 2nd, 4th, 9th & 11th 2025

Session 2: June 16th, 18th, 23rd & 25th 2025

Session 3: June 30th, July 2nd, 7th and 9th 2025

Session 4: July 14th, 16th, 21st and 23rd 2025

$575 plus HST

advanced dinghy

Prerequisities required: CANSail 1
Individuals 16+ years old

This program builds on our CANSail 1 level dinghy program and helps sailors to continue to develop their knowledge and sailing skills with more advanced training. Adult programs are taught in our dinghy class of 420s, accommodating 2 adults in each boat. The CANSail 2 program faces of teaching sailors to adjust their bodies and boats for changes in direction and wind speed while sailing, and to perform boat-handling maneuvers in a controlled manner while in a controlled setting. These skills are taught in both classroom and on-water practice by our qualified and experienced instructors. CANSail certificated are awarded upon successful completion of a set of practical skills and demonstrated knowledge at a CANSail 2 level.

This course is taught on Monday and Wednesday evenings in 2025 from 5pm – 8:30pm over 2 weeks; for 14 hours of sailing!

Session 1: June 30th, July 2nd, 7th and 9th 2025

Session 2: July 14th, 16th, 21st and 23rd 2025

$650 plus HST

start Keelboat

No prerequisites required CANSail 1
Individuals 16+ years old

This entry-level course is designed for individuals with little to no sailing experience who want to develop fundamental skills as crew aboard a keelboat. Participants will learn essential sailing terminology, boat handling, safety procedures, and basic seamanship while contributing to the operation of a keelboat in moderate daytime conditions. Training includes both on-water practice and classroom learning, covering topics such as wind awareness, sail handling, docking, and emergency procedures. Sessions focus on hands-on learning in a relaxed and supportive environment. Successful candidates will receive the Sail Canada Start Keelboat Sailing Standard certification.
These training sessions involve brief periods of moderate upper body effort and require a reasonable level of arm strength. Participants will be exposed to sun, wind, spray, and rain, with weather conditions varying based on the season. While underway, the vessel may move unpredictably due to wind and waves, and temperatures on the water may be cooler than on land.

This course is taught on Monday and Wednesday evenings in 2025 from 5pm – 8:30pm over 2 weeks; for 14 hours of sailing!

Session 1: June 2nd, 4th, 9th & 11th

Session 2: June 16th, 18th, 23rd & 25th

Session 3: June 30th, July 2nd, 7th and 9th

Session 4: July 14th, 16th, 21st and 23rd

$925 plus HST

Scroll