Sailing from VYC, Toby Heywood competes in the Western Cape dinghy circuit. Since October 2025, 13 races across 2 regattas have been recorded for Toby. Toby's primary class has been 505, with additional appearances in Hobie Tiger. Notable results include victory at the SailingSA events in the multiple fleets fleet and strong finishes at the SailingSA events. Toby remains active in regional dinghy racing.