Join The Oakville Yacht Squadron Sailing School Programs today

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.

Due to popular demand, many of our programs are now full. Please consider joining the waitlist, to complete a waitlist registration, you must enter a credit card number. But don't worry, we won't charge you unless a space opens up in the program.

Private & Group Lessons

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 23rd and June 29th and are customizable based on the interest of each group.  Please reach out to the Head Instruction at oysheadinstructor@gmail.com for program details and availability.  

These lessons are exclusively scheduled through contact with the Head Instructor. 

Wet Feet

RECOMMENDED FOR AGES 6-9
PREreQUISITES: NONE

The OYS Wet Feet program provides a safe, fun, and exciting introduction to sailing.  We recommend this program for kids 6 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 8:30am to 3:30pm.  Extended camp hours are available.

Cost per 1-week session: $450.00 (HST exempt)
Cost per 2-week session: $775.00 (HST exempt)

CANSail 1 & 2

junior program for ages 9-12
senior program for ages 13-18

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 in one or two week sessions Monday to Friday during July and August running from 8:30am to 3:30pm.  New this year, is our Junior and Senior program offerings.  Junior programs are recommended for ages 9-12 and Senior program is recommended for ages 13-18.  CANSail 1/2 is now offered as a 1 week program, we strongly recommend that you register in the 2 week session, as 1 week is not enough time to develop the skills required to achieve a level.  Extended camp hours are available.

Cost per 2-week session: $775.00 (HST exempt)

Cost per 1-week  session: $450.00 (HST exempt)

CANSail 3 & 4

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 a 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 8:30am to 3:30pm. Extended camp care is also available.

Cost for 1 month session: $1,400.00 (HST exempt)

Opti Learn to Race


PrereQUISITES: certificate in cansail 1
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 & 4.  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.

Offered in 4 week sessions in July and August, Monday to Friday, 8:30am-3:30pm. Sailors may elect to return for a second 4 week session.  Extended camp care is available.

Cost for 1 month session: $1,400.00 (HST exempt) + plus $500 Optimist Charter

Opti Race Team


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.

Offered as an 8-week session in July and August, Monday to Friday, 8:30am-3:30pm. Extended camp care is available.

Cost for 2 month session: $2,500.00 (HST exempt)

420 Double Handed Race Team

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.

This program is offered as an 8 week session in July and August running from 8:30am to 3:30pm.

Summer Season: $2,200.00 (HST exempt) + $600 charter

Laser Race Team

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.

This program is offered as a 14-week program which includes Spring training May through June, and an 8-week session in July and August running from 8:30am to 3:30pm.

Spring & Summer Season: $3,100 (HST exempt)

Extended Camp Care

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.

Cost: $120.00/week

All programs includes the $19 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.

Refund Policy: 5% administration fee will be deducted from the refund from the time of registration until 30 days before the program start date. A 75% refund will be issued if the reservation is cancelled between 29 days and 7 days fo the program start date. 50% refund will be issued if the reservation is cancelled within 6 days of the program start date unless a medical document is provided.  Applicable discount codes must be entered at the time of purchase, OYS cannot retroactively apply any discount codes.​