Adult Sailing School – Oakville Yacht Squadron

2026 Registration opens on January 5th at 12 noon

Adult Sailing Programs

Our Adult Sailing Programs offer a safe, supportive, and fun environment to learn on dinghies or keelboats

Our programs focus on hands-on time on the water, skill development, and confidence building following the CANSail circulum (dinghy) and Basic Cruising Certification (Keelboat).

With small class sizes, expert instruction, and the beautiful setting of Oakville Harbour, you’ll enjoy personalized coaching, plenty of sailing time, and an unforgettable summer experience—on and off the water.

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.

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.

Evening Sessions:

This course is taught on Monday and Wednesday evenings in 2026 from 5pm – 8:30pm over 2 weeks.

Session 1: June 22nd, 24th, 29th, and July 1st 2026

Session 2: July 13th, 15th, 20th and 22nd 2026

Session 3: August 3rd, 5th, 10th and 12th 2026

$650 plus HST

basic cruising

No prerequisites required
Individuals 16+ years old

OYS Basic Cruising is the ideal entry point for sailors looking to take the helm of a cruising keelboat with confidence. Based on the Sail Canada Basic Cruising Standard, this course builds the skills needed to safely skipper a keelboat in familiar waters during daytime, light to moderate wind conditions. You’ll learn to operate the boat under both sail and power, developing essential seamanship skills as crew and skipper.

Through hands-on instruction, participants gain experience with sail handling, learn sailing terminology while practicing these skills, safety equipment, weather awareness, docking and maneuvering in a sailboat, and basic navigation using charts. On-shore teachings will complement on-water skillsets. This course provides a strong, practical foundation for enjoying keelboat sailing safely and responsibly. Basic Cruising certification is awarded upon successful exam and demonstration of practical sailing skills. Participnts should anticipate 18 hours of sailing and 10 hours of theory.

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.

Week Long Session:

This course is taught Monday to Friday from 9:30 am – 3:30pm over 1 week.

Session 1: June 15th – 19th 2026

$950 plus HST

Evening Sessions:

This course is taught on Monday and Wednesday evenings in 2026 from 5pm – 8:30pm over 4 weeks.

Session 1: May 25th, 27th, June 1st, 3rd, 8th, 10th, 15th and 17th 2026

Session 2: June 29th , July 1st, 6th, 8th, 13th, 15th, 20th and 22nd 2026

Session 3: August 3rd, 5th, 10th, 12th, 17th, 19th, 24th, and 26th 2026

$950 plus HST

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