Our Amazing Coaches


Annika Hambleton

Head instructor

Annika Has been sailing at OYS for as long as she can remember, she has been a part of the wonderful family of coaches at the sailing school for the past 4 years. This year Annika is excited to return as the Head Of Learn To Sail here at OYS for the second year in a row, and is looking forward to working with such a wonderful group of instructors and athletes. Annika is looking forward to passing on the love of sailing to the new generations of athletes, and another stellar summer at the club! Annika has just finished her second year at Seneca college for Fashion Design. Her passion for sailing and the water spreads into her everyday life with her desire to turn discarded textiles into newly loved and unique designs!

Jack Bruce Bio Photo

Jack Bruce

Head race Coach

Jack Bruce is this year’s new head race coach. He spent the last seven summers coaching laser race teams around the lake and racing on keel boats in his spare time. Last year he became a Learning Facilitator for Sail Canada and now certifies new instructors each spring. He also just graduated from Teachers College at Brock University. His vast sailing, coaching and teaching experience will be a great asset to our OYS race program.


Liam Bruce

Laser coach

Liam is a trained Competition Development Coach with extensive racing experience. He has been a member of the national team since 2018 and some notable results include winning ILCA Canadians 2x and finishing 3rd at the 2024 North American ILCA Championships in an ILCA 7. Outside of sailing he enjoys golf and cycling.

Matthew Tiplady Bio Pic

Matthew Tiplady

420 race coach

Matt began sailing at a young age in the Wetfeet Program at OYS and progressed through the levels, eventually joining the Ontario Sailing Team where he competed in various local, national, and international regattas with numerous podium finishes. Matt has worked at OYS for the last four summers, running the double-handed race team, CANSail 3/4 program, adult sailing programs, and private lessons for families and kids of all ages and levels of experience. Along with his deep passion for sailing, Matt also enjoys music and playing guitar. He is excited to be returning for a third season as our double-handed race team coach, and to continue sharing his knowledge of sailing technique, race strategy, and the C420 class with the next generation of sailors in Oakville.

Daniella Bio Photo 2024

Daniella Woodbridge

Opti Race Team

Daniella Woodbridge is our Opti Race Team coach for the 2024 summer! Daniella is currently doing her undergraduate degree in mechanical engineering at the University of Miami and is an active UM sailing team member. She has also been a part of the OYS community for 11 years starting her sailing journey in the Opti Learn to Race Program. Since then she has raced Laser ILCA 4, ILCA 6, flying juniors and i420s classes. During her 6 years as a laser sailor, Daniella was also a part of the provincial development team. Daniella is super stoked to use her experience and passion to help develop the skills of her sailors this season!

Cole Bio Photo

Cole Redwood

Cansail 3 & 4 coach

Meet Cole, a distinguished sailor whose dual passion for the sea and the sky sets him apart. Beginning sailing at the age of 8 sailing Echo’s transformed to many years sailing C420s. Cole was an enthusiastic and successful member of the 420 double-handed race team at the Oakville Yacht Squadron competing at multiple regattas during the summer season. Additionally, Cole loves to help out as part of the Race Committee at local regattas hosted by the Club. His deep fascination with aviation and weather adds depth to his knowledge and love for the sport. He enjoys blending an understanding of the atmospheric conditions with sailing tactics, to create a fun and safe sailing experience! </>

Kylie Laretei

Kylie Laretei

Cansail coach

Kylie grew up sailing at the OYS on her grandparents boat, and then at the sailing school. Now returning for her fourth year as an instructor, she brings her experience and enthusiasm to share with the next wave of sailors. When she’s not sailing, you may find her on ice, playing hockey, swimming, or taking part in other outdoor sports. Kylie is also going into her second year as an engineering student at McMaster University.


Mathias Basen

CANsail coach

Mathias grew up learning to sail at the OYS sailing school, and he is looking forward to joining the Wetfeet team for the first time this summer. Since 2022, Mathias has been a part of our C420 and Laser race teams. Mathias will start Grade 12 at Oakville Trafalgar High School in the Fall. When not sailing, he enjoys playing football and rugby at school, and true to his Norwegian roots, he loves to ski.

Nicolas Bio Photo 2024

Nicolas Prete

CANSail Coach

Nicolas took his first sailing class at OYS Sailing School when he was 11 years old. Since then, he completed CANSail 6 and was on the 420 race team for 2 years. He can’t wait to spend the summer on the water coaching young sailors. When he is not sailing, he is studying civil engineering at York University.

Mostafa Bio Photo

Mostafa Arafa

CANSail coach

Mostafa is a student at Iroquois Ridge High School that will start his second year coaching this summer. He has been sailing for years and was even a participant in both the Opti race team and the 420 race team at OYS. He also likes to play basketball, soccer and footballHe is eager to share his passion for the sport and help everyone continue their sailing journey.

Anna Bio Photo 2024

Anna Loiselle

CANSail coach

Hello, everyone! I’m thrilled to be back for my second year coaching CANsail 1&2 at the Oakville Yacht Squadron sailing school. Sailing has been my passion for years, and I’ve had the privilege of competing in numerous regattas as part of the C420 race team at OYS. Recently, I embarked on an incredible journey that allowed me to sail around the world while completing my grade 11 with the Class Afloat program. Now that I’m back home, I can’t wait to share my love for sailing and all the valuable lessons I’ve learned with our enthusiastic young sailors! 

Habiba Bio Photo

Habiba Arafa

cansail 3 & 4 coach

Habiba’s love for sailing began almost 10 years ago when she started sailing in Qatar, she then joined OYS as part of the 420 race team where she participated in many regattas. IN the fall, Habiba is headed into her second year of studying Medical Sciences at Western University. She is excited to come back as this years CANsail ¾ coach and have another great summer! .

Samantha bio photo

Samantha Dwivedi

Opit learn to sail coach

Meet Samantha! She is very excited to be coaching the Opti learn to race team this year. Samantha has been sailing for 6 years now and has spent the past two summers racing in the laser radial. Though this is her first year coaching racing she has been coaching soccer for the past 4 years and loves it. A fun fact about Samantha is that this September she will be headed out west to California to study Neuroscience.


Nicolai Basen

CANSail coach

Nicolai learned how to sail at the OYS Sailing School after he moved to Oakville. He has taught both WetFeet and CANSail 1/2 for the past three years. Nicolai can’t wait for the summer to start, and he looks forward to meeting everyone and sharing his love of sailing in the safe and friendly environment of the sailing school. Nicolai has just finished his second year at Queen’s University where he is taking Geological Engineering. When Nicolai isn’t at OYS, you will find him on the golf course or at his cottage.