The Oakville Yacht Squadron Sailing School has been proudly serving the Oakville community since 1965, teaching many children and young adults to sail at our great waterfront setting.
RECOMMENDED FOR AGES 7-9
PREreQUISITES: NONE
The OYS Wet Feet program provides a safe, fun, and exciting introduction to sailing. We recommend this program for kids 7 years old to 9 years old. Our program introduces these young sailors to fundamental sailing skills including balancing the boat, steering, rigging and de-rigging the boat and tacking. The Wet Feet program makes use of our extremely stable fleet of Optimist dinghies. For a balanced program, kids can expect their days to be filled with games and activities to compliment their newly learned sailing knowledge. Kids can expect to participate in a variety of games and activities to complement their newly learned sailing knowledge. This program is offered as a one or two week session, Monday through Friday throughout July and August running from 9:00am to 3:30pm. Extended camp hours are available.
1-week session: $550
2-week session: $1025
Programs start Monday, June 29th 2026
junior program for ages 9-12
senior program for ages 13-16
PREreQUISITES: NONE
The CANSail 1 & 2 introductory program focuses on fun, safety and fundamental sailing skills. Sailors will learn skills including boat balance, sail trim, heading up, tacking, gybing, leadership, knots, basic weather patterns, docking and sailing terminology. These skills are creatively crafted into fun and unique lessons by our team of qualified and experienced instructors both on and off the water. The CANSail 1/2 program is taught in our fleet of RS Fevas and Quests; these vessels are known for their stability on the water, and easy maneuverability; excellent learning vessels. Programs are offered as two week sessions Monday to Friday during July and August running from 9:00am to 3:30pm.
Junior programs are recommended for ages 9-12 and Senior program is recommended for ages 13-18. Extended camp hours are available.
Available as a 2-week session: $1025
Programs start Monday, June 29th 2026
PREREQUISITES: certificate in cansail 1 & 2
CANSail 3 & 4 progressively builds and develops the skills in CANSail 1 & 2, with a focus on keeping the sailor engaged with appropriate learning opportunities. The CANSail 3 & 4 program is privileged to use our large fleet of 420 dinghies. The 420 dinghies are performance boats sailed double handed being stabile at higher speeds and a modest sail area make this vessel ideal for racing. This program focuses on teamwork, boat balance and steering in various conditions, appropriate sail trim for accelerating and stopping, sailing upwind, rounding marks via gybing and tacking, tactics and strategy in regatta participation and seamanship. Our instructors develop engaging lessons that help to build these skills whilst providing an exciting day of on the water sailing activities. CANSail 3/4 is exclusively offered as a 4-week session; at the upper level of programming it does take longer to develop the skills need to achieve your sailing level.
In this program, there is a requirement for local regatta participation. Regatta participation is a highlight for our sailors in this program, and parental support is needed for chaperoning, hauling trailers, travel planning and regatta assistance. Please note that regatta fees and travel expenses are not included in the program fee, however, coaching will be provided at regattas.Programs is offered as a 4-week sessions Monday to Friday during July and August running from 9:00am to 3:30pm. Extended camp care is also available.
Offered as a 1-month session: $1,825
Session 1: June 29th – July 24th 2026
Session 2: July 27th – August 21st 2026
PREREQUISITES: certificate in cansail 4
This is a brand new course at OYS!
Take your sailing to the next level with our Trapeze & Spinnaker course — designed for confident sailors ready for some excitement and teamwork! This advanced program introduces sailors to the thrill of doublehanded sailing with trapeze and spinnaker equipment, combining balance, communication, and precision, while working towards obtaining their CANSail 5 in the double-handed 420.
Sailors will learn how to fly the spinnaker for speed downwind, master wire-to-wire tacks, and experience the exhilaration of sailing out on the trapeze. Lessons focus on safety, coordination, and fine-tuning boat handling for performance sailing. Each day on the water brings new challenges and skills — from setting and trimming the spinnaker to maintaining perfect balance while planing and surfing.
While this is not a race-focused program, sailors will have the opportunity to put their skills into practice by attending one local regatta. The emphasis is on fun, teamwork, and skill development rather than competition — giving sailors the confidence to enjoy fast, exciting sailing in a supportive environment.
Offered as a 1-month session: $1,825
Session 1: June 29th – July 24th 2026
Session 2: July 27th – August 21st 2026
PrereQUISITES: certificate in cansail 2
recommended for sailors 9-14 and max weight 120 lbs
requirements: sailors must charter an opti from Oys or supply their own boat. program fee includes session storage
In the OYS Opti Learn to Race program, sailors will be working to achieve their CANSail 3. The Opti racers continue to develop their skills by introducing a new racing aspect. Sailors will learn leadership, boat balance and steering in various conditions, hiking, appropriate sail trim for desired destination including accelerating and stopping, sailing upwind, rounding marks via gybing and tacking, and race tactics and strategy; all with a focus surrounding racing. Sailors in this program are required provide their own Optimist dinghy, charters are available through the OYS Sailing School. We recommend this program for sailors 9 thorough 14 years old, with a maximum weight of 120 pounds.
The Oakville Yacht Squadron is a sailing centre of excellence for racers in the GTA. To maintain this level of excellence, a higher level of commitment from our racers and parents is required. Regatta participation is a highlight for our sailors in this program and parental support is required by way of chaperoning, hauling trailers, travel planning and regatta assistance. Please note that regatta fees and travel expenses are not included in the program fee. Coaching will be provided at regattas.
Unfortunately, discount codes are not available on charters.
Offered in 4-week sessions in July and August, Monday to Friday, 9:00am-3:30pm. Extended camp care is available.
Offered as a 1-month session: $1,825
Limited charters will be available: $650 plus HST
Session 1: June 29th – July 24th 2026
Session 2: July 27th – August 21st 2026
PrereQUISITES: certificate in cansail 3
recommended for sailors 9-14 and max weight 120 lbs
requirements: sailors must supply their own boat. program fee includes session storage
In the OYS Opti Race program, sailors will be working to achieve their CANSail 4. The Opti racers continue to improve their skills through more competitive racing. Sailors will continue to learn and improve their leadership, boat balance and steering in various conditions, hiking, appropriate sail trim for desired destination including accelerating and stopping, sailing upwind, rounding marks via gybing and tacking, and race tactics and strategy; all with a focus surrounding racing. Sailors in this program are required provide their own Optimist dinghy. We recommend this program for sailors 9 thorough 14 years old, with a maximum weight of 120 pounds.
The Oakville Yacht Squadron is a sailing centre of excellence for racers in the GTA. To maintain this level of excellence, a higher level of commitment from our racers and parents is required. Regatta participation is a highlight for our sailors in this program and parental support is required by way of chaperoning, hauling trailers, travel planning and regatta assistance. Please note that regatta fees and travel expenses are not included in the program fee. Coaching will be provided at regattas.
Junior sailors in the Opti Race Program must provide their optimist. Program fee includes session storage.
This program is offered as an 8-week summer session in July and August OR a 4-week session in July or August. Programs run Monday through Friday from 9:00am to 3:30pm. Many regattas occur on the weekend, which may alter the the weekday programming to ensure rest days for our athletes. Extended camp care is available.
8-week Summer Session: June 29th – August 21st 2026 $3,250
4-week July Session: June 29th – July 24th 2026. $2,112.50
4 week August Session: July 27th – August 21st 2026 $2,112.50
Spring Training: $750
Spring training will occur in May and June. Spring training courses will be depended based on registration numbers and scheduled based on participant availability.
PREreQUISITES: certificate in cansail 4
requirements: Must charter 420 from oys or supply their own boat.
In this program, the advancing sailors’ skills are enhanced and applied to sailing faster and competitively. Sailors will be working towards completing their CANSail 5 & 6. These enthusiastic sailors will experience more challenging training sessions while mastering and combining previously learned skills in a race focused environment. This program focuses on fine tuning the sailors’ sailing proficiency. Sailors will learn imperative racing skills including optimal body position in all conditions, powering up and depowering using sail controls, sheeting and steering, tactical mark rounding, gybing and tacking in all conditions, and stopping and starting on a line. Sailors in this program are required provide their own 420 dinghy, whether owned or privately chartered. Summer storage is included in the registration fee.
The Oakville Yacht Squadron is a sailing centre of excellence for racers in the GTA. To maintain this level of excellence, a higher level of commitment from our racers and parents is required. Regatta participation is a highlight for our sailors in this program and parental support is required by way of chaperoning, hauling trailers, travel planning and regatta assistance. Please note that regatta fees and travel expenses are not included in the program fee. Coaching will be provided at regattas.
Unfortunately, discounts after not offered on charters. This program is offered as an 8-week summer session in July and August OR a 4-week session in July or August. Programs run Monday through Friday from 9:00am to 3:30pm. Many regattas occur on the weekend, which may alter the the weekday programming to ensure rest days for our athletes. Extended camp care is available.
8-week Summer Session: June 29th – August 21st 2026 $3,225
4-week July Session: June 29th – July 24th 2026. $2,069
4 week August Session:July 27th – August 21st 2026 $2,069
420 8-week charters are available: $1,050 plus HST
Spring and Fall training sessions may be offered if there is considerable interest.
PREreQUISITES: certificate in cansail 1-4
requirements: sailor must supply their own boat. Program fee includes summer storage.
In this program, the advancing sailors’ skills are enhanced and applied to sailing faster and competitively. Sailors will be working towards completing their CANSail 5 & 6. These enthusiastic sailors will experience more challenging training sessions while mastering and combining previously learned skills in a race focused environment. This program focuses on fine tuning the sailors’ sailing proficiency. Sailors will learn imperative racing skills including optimal body position in all conditions, powering up and depowering using sail controls, sheeting and steering, tactical mark rounding, gybing and tacking in all conditions, and stopping and starting on a line. Sailors in this program are required provide their own Laser dinghy, whether owned or privately chartered. Summer storage is included in the registration fee. There is one Laser Radial dinghy available for charter through the OYS Sailing School. The Oakville Yacht Squadron is a sailing centre of excellence for racers in the GTA. To maintain this level of excellence, a higher level of commitment from our racers and parents is required. Regatta participation is a highlight for our sailors in this program and parental support is required by way of chaperoning, hauling trailers, travel planning and regatta assistance. Please note that regatta fees and travel expenses are not included in the program fee. Coaching will be provided at regattas.
his program is offered as an 8-week summer session in July and August OR a 4-week session in July or August. Programs run Monday through Friday from 9:00am to 3:30pm. Many regattas occur on the weekend, which may alter the the weekday programming to ensure rest days for our athletes. Extended camp care is available.
8-week Summer Session: June 29th – August 21st 2026 $3,995
4-week July Session: June 29th – July 24th 2026. $2,569
4 week August Session: July 27th – August 21st 2026 $2,569
Spring Training: $850 plus HST
Fall Training: $750 plus HST
Spring training will occur in May and June. Fall training will occur in September and October. Training courses will be depended based on registration numbers and scheduled based on participant availability.
Available for sailors who need to be dropped off or picked up outside of our regular hours. The OYS Sailing School Program is flexible for those guardians who need to take some extra time. Extended hours in the morning will begin at 8:00 AM and in the afternoon be offered from 3:30 – 5:00 PM.
Offered in 1 week sessions
$150 per week
PREreQUISITES: NONE
Whether you are looking to try a new sport, a family activity, to complete a level before the summer starts or team building for a company, the OYS Sailing School has something for you!
A limited number of private and group lessons will be available between May 20th and June 18th and are customizable based on the interest of each group – suitable for ages 7 to 77. Please reach out to the Head Instructor at oysheadinstructor@oysqn.com for program details, pricing and availability.
These lessons are exclusively schedule through contact with the Head Instructor.
All programs includes the $24 Ontario Sailing fee, which provides the OYS Sailing School the framework to plan captivating sailing programs consistent with the Sail Canada sailing levels of prescription. Program prices are subject to change without notice.
Refund Policy: 10% administration fee will be deducted from the refund from the time of registration until 60 days before the program start date. A 75% refund will be issued if the reservation is cancelled between 59 days and 30 days of the program start date. A 50% refund will be issued if the reservation is cancelled between 29 days and 15 days of the program start date. Unfortunately, we cannot offer refunds within 14 days of the session start unless a medical document is provided within 72 hours of withdrawal.
Applicable discount codes must be entered at the time of purchase, OYS cannot retroactively apply any discount codes. Discount codes do not have any cash value and cannot be transferred. Discounts are not available on charters. In the event of injury, a pro-rated refund will be calculated, and the participant will be offered the pro-rated refund. Participants asked to leave courses due to safety or disciplinary concerns shall not receive a refund of any funds paid to participate in the course.
