A Western Cape sailor, Diego Charleston represents KYC in competitive dinghy racing. Diego's competitive record on SailingSA begins in December 2025. Since then 18 races across 2 regattas have been completed. Diego's primary class has been RS Tera Sport, with additional appearances in other fleets. Diego's best results include winning the SailingSA events in the multiple fleets fleet, as well as the SailingSA events in the multiple fleets fleet. Diego remains active in regional dinghy racing.