Oscar Chalupsky
CEO, Nelo Kayaks and Surfskis

Guest Instructor

Surf Ski, Paddling


Oscar Surfski Clinic - Private Session

Private Session with Oscar Chalupsky

Learn new skills or work on your current technique.

Please email info@vkoc.net with any requests or comments

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  • Limited Availability
Group Clinic with Oscar Chalupsky

Starts at 9am Surf Skis are available for rent if you do not, or cannot, bring your own.

Class is approximately 3-hours

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Meet & Greet Oscar Chalupsky, Nutrition Talk, Dinner

Join Oscar for an evening discussion on sports nutrition for paddling and racing. The grill will be going with delicious dinner options. Feel free to bring your own beer or wine. Just drink responsibly.

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Oscar Chalupsky - South Africa



OSCAR CHALUPSKY (South Africa) -Twitter: @Oscar Chalupsky


  • Born: 1963, Sports: ocean ski paddling, kayaking (sprint and marathon), surf life saving
  • Represents: South Africa
  • Results: 12 x Molokai winner, multiple winner of the Sella Descent, Lucky Strike Challenge and Umkomaas River Marathon
  • VP, of Epic Kayaks until 2015
  • CEO, Nelo Kayaks


Oscar Chalupsky is one of the most decorated and recognizable watermen in the world. His resume spans over an incredible 36 years, with few paddlers holding a record comparable to this. His effortless technique and knowledge of the ocean has seen him achieve results some athletes can only dream of including 12-time Molokai Ocean Ski Champion, multiple winner of the Umkomaas River Marathon and 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, Oscar 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. Oscar came second in 1981 with Matt Carlisle. With his brother Herman he had five top 3 finishes.


The above already would take a 'normal' elite athlete several lifetimes, but Oscar also won the Lucky Strike Challenge 10 times. This endurance feat started as a friendly challenge on January 7, 1972, between ultra-distance runner John Ball and Surf Lifesaving legend John Woods, who would paddle the race, where the outcome would indicate who was faster - the runner or the paddler? The Challenge is the ultimate contest between man and the elements of nature, a reputation that has enticed competitors back every time it has been staged.

Away from the competition arena Oscar has played a vital role in the development and success of Ocean Ski Paddling. In 2000 Oscar co-founded Epic Kayaks, which today is one of the leading brands in Ocean Ski Paddling. In May of 2015 Oscar stepped down from his position with Epic and took over as the CEO for Nelo Surfski, which is currently the worlds largest kayak manufacturer.

Oscar’s many successes have inspired the paddlesports world and left people wondering how he does it. In a bid to answer these questions Oscar conducts surf ski 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, he has left an everlasting impression on this community.

Oscar Chalupsky 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 and for this Oscar is a deserving nominee for the Lifetime Achievement award.


Other achievements:


  • 1978: Junior and Senior Surfski champion, Junior and Senior Iron Man champion. Both in South Africa.
  • First person in the world to win junior and senior Iron Man about one month before Grant Kenny.
  • 8 South Africa Iron man titles and 12 Senior surf ski titles.

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