The 2018 GREAT OPTIMIST RACE was incredible!

The inaugural race took place on Sunday 21 October 2018 in gusty and tricky conditions on a beautiful day in Cape Town. 42 Optimist sailors set off on a tricky 3 lap course through the V &  A Waterfront, watched by 1000s of spectators. With the magnificent backdrop of Table Mountain, the sailors raced for glory and survival. The competitors comprised of adults made up of medical survivors, local celebrities, Captains of Industry and some pro sailors. Three separate start, beginner, intermediate and pro sailors, allowed for a good handicap and a chance for those who had only learned to sail days before. This unique race was all about overcoming the odds and surviving. It’s about inspiring sick and needy kids to never ever give up and find a passion to live for. So, as in the race of life, this race had some unique curveballs and obstacles for the sailors to overcome. Not only did the wind squalls and gusts in the second basin cause havoc, but so did the pedestrian bridge that opened and closed at will, along with “water pistol armed and dangerous” local celebrities Kieno Kammies and Tanya Neft on their own bigger yacht. These were the disrupters. The competitors had to get past these to cross the line.

Our Brave Survivors, Caleb and Jasper, neck and neck for 1st Place!

    It was Caleb Swanepoel, an amputee and shark attack survivor (in the Primi Piatti Optimist) who sneaked in to win the race, just ahead of Jasper Eales in the Sealand Optimist.  (Jasper is a liver transplant survivor).


First to sink – Ian Klopper of NSRi in the web tickets Optimist. Jumping the start award – Arno Carstens ( Rock Star). Most committed to the cause and in 3 rd Place – Maryke Musson of the 2 Oceans Aquarium. What a race and what a day! During the 3 days – the Little Optimist Trust hosted sailing experiences and academy’s for kids in less fortunate circumstances. Reach for a Dream kids and their parents got to experience sailing, a captain courage ceremony, the 2 oceans aquarium and lunch at a restaurant. Law hill academy kids and  9 mile project kids were also treated to a day at the boat show, which included all of the above. Fun was had, passion was found, skills were taught and dreams were made real! And that’s what it’s all about. All Optimists will be used in the new Little Optimist Sailing Academy being set up to teach sick and needy kids how to sail. To assist, donate, sponsor a boat or donate a boat, please contact

For a visual representation of how the day went, check out the video below:


Our Winners Of The Day



Our Survivor Squad

Our Racers For The Day

PR Value The Little Optimist 2019

WOW The Little Optimist outdid itself this year - please see the link to the Newsclip report below. An AVE of R1 521 955, 56 in media coverage for the 2019 Little Optimist Race! (PR VALUE R4 565 866) achieved!  Click here for full article

Smooth sailing at the Optimist Sailing Academy

At The Little Optimist Trust we are passionate about sailing therapy and our presence at The Cape Town International Boat Show was another opportunity for us to bring kids down to the water and get them sailing. We hosted children from Reach for a Dream, 9 Miles...

More on the Cape Town International Boat Show 2019

Pippa in conversation with Greg Bertish, a big wave surfer, a sailor, a lifesaver, and the founder of theLittle Optimist Trust and organiser of this race. Listen below

‘Voice’ winner Craig Lucas to swop mike for Great Optimist Race boat

Cape Town – Voice SA season 2 winner Craig Lucas will swop his microphone for a boat when he sails an Optimist (children’s dinghy) in the Great Optimist Race at the V&A Waterfront tomorrow. His mission is to raise funds and awareness for charity. Lucas is an...

South African shark-attack survivor sails to victory

Shark-attack survivor Caleb Swanepoel showed disability is no match for determination when he claimed the Great Optimist Race winner title for the second year in a row at the V&A Waterfront this Saturday. The Stellenbosch University student, who has a prosthetic...

Disability not an impediment as Caleb Swanepoel wins Great Optimist boat race

Cape Town – Shark attack survivor Caleb Swanepoel showed disability is no match for determination when he claimed the Great Optimist Race winner title for the second year in a row at the V&A Waterfront on Saturday. The Stellenbosch University student, who has a...

E-news The Great Optimist Race

On the Yellow Couch: Josie Borain on competing in the Great Optimist Race

Joining Pippa on the yellow couch is Josie Borain, a woman who’s enjoyed success on both sides of the camera, initially as South Africa’s first international supermodel, then later as an acclaimed photographer.  

Optimist Sailing SA team

Well done Optimist Sailing SA team keep up the good work! Well done Sean Kavanagh who came in 4th place - we are so proud. Follow the link toe todays results…/d…/races/race-resultsall

Getting ready for The Great Optimist Race

We are getting ready and ship shape for #thegreatoptimistrace 2019. Huge prep and boat fixing and beautifying being done by our amazing experts @johnhishin @drumbeatphotography @capetownsportphotography Zeekoe Vlei Yacht Club Massive thanks...

The Highlights Of The Day

Great Optimist Race Gets R4.3 Million Worth of Free PR


To Our Main Sponsors, THANK YOU!





It’s official!

We are proud to announce that The Great Optimist Race will take place at the Cape Town International Boat Show on 20 October 2018, at 12 noon.

Your company ( or You) can have your own Yacht, representing your brand, getting huge exposure and doing so much good for sick and needy kids.

The Little Optimist Trust will be hosting the race, along with other events and a sailing academy over all 3 days of the Boat Show. (19, 20, 21 October, all day with high visibility).

This is going to be a national showcase underneath Table Mountain, and in front of 1000s of spectators, boat owners, celebrities and the public.

The race and event will be covered by and will feature on TV, radio,  print and Social Media, and a short Documentary movie will be made.

More importantly, it will be inspiring many, and raising funds and awareness for needy charities and sick kids.


Entry Fees / Rental and sponsorship options in the document below.

Sponsored and donated Optimist boats will go on to teach sick and needy kids to sail through the Little Optimist Sailing Academy, for many years to come.

Sponsored and entered boats will be raced by you or your representative, celebrities, sports stars, CEOs & captains of Industry, past survivors, dads and moms.

Other charity boats will be racing alongside you and representing organisations like NSRI, The Children’s Hospital Trust, Cape Town Tourism, Cancer Dojo, Reach for a Dream, and more…..

All donations are section 18a Tax deductible.

There will be +/- 40 Optimist boats racing.  All skippered by adults, all raising funds and awareness for little sick and needy kids.

Please see the proposal for an Optimist sponsor below, and let me know if I can sign you up for this donation or sponsorship, or if you need to chat or get a  bit more info, please feel free to contact us:

All donations are section 18a Tax deductible.

Click Here To Download Proposal