Our two main events of the year are The Great Optimist Race (TGOR) and our Wine Auction.

Please see the tabs below for more information on the events.

Our main fundraising event annually is The Great Optimist Race.  40 Optimists participated in the inaugural event, held during the 2018 Cape Town International Boat Show.

The format is as follows:

  • Many of the Optimists are sponsored by a company
  • Most Optimists sail to raise money for a charity of their choice
  • A Minimum of 20 Optimists will be sailed by either a Survivor, a Champion of Industry or Celebrity as skipper.

The first event was an overwhelming success despite a few logistical challenges. We have already put plans in place for 2019 to make this an event better, bigger and more fantastic! The interest has been phenomenal. To relive the magic, click here.

In 2018 we raised close to R250 000 through sponsorship to purchase, upgrade and repurpose dinghies for a new sailing academy. We also raised R100 000 for our charities, which included NSRI, Sharkspotters, Newborns Trust, Two Oceans Aquarium and The Little Optimist Trust.  This year we plan to raise R500 000 for charity.

We also hosted a number of events for our social partners and NPOs: Reach for a Dream, 9 Miles Project and Lawhill Academy.  We aim to make this a bigger part of what we do in 2019 and going forward. We will teach, inspire and give more underprivileged and sick kids a sailing experience, hope, passion and new skills this year.

The Great Optimist Race received PR Coverage to the value of R4.3 Million. Highlights included television coverage on Espresso TV and ENCA TV, and our partnership with Cape Talk Radio to publicise the event. In addition, the event received social media coverage, as well as publicity in Newspapers, Magazines, Radio and on line in the run -up to the main event by way of a number of Great Optimist Race – related activities.  (see PR report)

The Great Optimist Race 2018

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. 

The  Great Optimist Race 2019  was held during the Cape Town International Boat Show, on October 19th at 12 o’clock.  40 Optimist Children’s dinghies were raced by adults ( Celebrities, Medical Survivors & Captains of Industry)  not only for glory, but also to raise money and awareness for the charity of their choice . The Race is a FANTASTIC and UNIQUE fundraising event , spreading Optimism and Hope across so many sectors. All the funds raised by each boat will be split between The Little Optimist Trust and the charity supported by that boat.


Charities Represented at The Great Optimist Race

The Great Optimist Race will be taking place on October 19 in the V & A Waterfront, during the Cape Town International Boat Show.  It is one of the most unique and fun charity events in the country, raising awareness for The Little Optimist Trust and all of the charities participating in the race this year. It is also a major fundraising event and we hope to raise R500 000 this year for all the charities involved.

For 2019 all our Optimist boat sponsors are partnered with a charity of their choice. These are the charities involved in the 2019 Race:


All photos by John Hishen at  @capetownsportphotography


Video by John Hishen at  @capetownsportphotography



Please take a read through the PR Report for the 2019 Great Optimist Race.


We challenged you, your friends, your family, your colleagues, your kids, and any sailor in South Africa and the world to sail an Optimist Dinghy for charity.

The Little Optimist Global Challenge  took place from 9-18 October 2020

Over 300 adults and kids entered, climbed into Optimist Dinghies, raised funds for charity,  had fun, and helped inspire at-risk youth.

We raised over ZAR240 000 for 14 charities, had 13 activations, gave sailing lessons and sailing therapy to 70 at-risk youth, and created boatloads of OPTIMISTIC  PR to the value of ZAR 5.7 million.   

Optimist Sailing is one of the biggest sailing classes in the world – there is a network of more than 150 000 registered Optimists in 120 countries around the globe.
Many of us — including great sailors, CEOs, sportspeople, celebrities, moms, dads, and kids around the world – first learned to sail in an Optimist Dinghy,
and these fantastic little boats still hold a special place in many of our hearts.

See, the photos, the videos, and the thrills, spills and SMILES on our Challenge site 

NOW you too can enter our Challenges for Charity anytime in 2021 – Watch this space!

To get involved in your own Challenge for Charity and for our TRUST, contact us for more info  


Due to Covid we are unable to hold our annual event – Paddle for Presents.

This event is the main drive to get teddies in for kids in hospital over Christmas.

This year we ask that you still donate at one of our drop off points.

Pay via SnapScan, Zapper, Eft, or cc – reference TOY – CLICK HERE

Drop off points:

    • HIIT Fitness – Parklands
    • Kom Surf – Kommetjie
    • SUP Cape Town – Battery Park
    • Clifton Lifesaving Club
    • Llandudno Lifesaving Club
    • Wetsuit Warehouse
    • Cape Town Surfing
    • Lifestyle Surf Shop – Muizenburg