Oscar Chalupsky   Coach Chalupsky

Oscar conducts paddling clinics around the world which teach paddlers how to train, race and win using his methods and technique. With thousands of people already beneficiaries of Oscars expertise,
. Oscar is larger than life, a legend, and known for his particular sense of humour; the way he is able to light up a room with his energy and passion. Oscars service to the paddlesports community has already spanned over 36 years and lucky for us, there is no signs of him slowing down!


Born: 1963, National Teams Surfski, Kayaking (sprint and marathon), Surf life saving, Waterpolo.
12 x Molokai World Surfski Champion
He is one of the most decorated and recognisable watermen in the world. His resume spans over an incredible 37 years, with few paddlers holding a record comparable to this. His effortless technique and knowledge of the ocean has seen him achieve results unheard of, as well as being an Olympic representative.

What’s outstanding about Oscar is his longevity and tenacity which has seen him take on and beat athletes over 30 years his junior. In 2012, at 49 years of age, He took home his 12th Molokai title, 29 years after his maiden win. A truly inspiring result.

On top of his ocean ski successes Oscar competed at the 1992 Barcelona Olympic Games where he was the team captain for South Africa. He is also a multiple winner of the prestigious Umkomaas River Marathon.

Oscar won the world-famous Sella Decent in Spain in 1986 with his brother Herman. The biggest marathon race that everybody wants to win! His father won the same race in 1968 and both their names are carved into the bridge over the Sella..

The above already would take a 'normal' elite athlete several lifetimes, but He also won the Port Elizabeth to East London surfski challenge of 240km 10 times. 
He conducts surf ski clinics around the world which teach paddlers how to train, race and win using his methods and technique.



Preferred Athlete Levels

Beginner, Intermediate, Advanced, Professional


1-on-1 Coaching, Consultations, Group Coaching, Local Coaching, Remote Coaching, Strength Training, Nutrition, Training Camps

Sport Types

Road Cycling, Swimming, Personal Training, Rowing



Athlete Requirements

Passion for paddling


390 Pedro Nunes Road