Hylton started sailing at the age of eight and went on to earn Western Cape, Eastern Cape and Natal colours. He also represented South Africa in many international events.
In 2007, Hylton bought his first keelboat, a Pacer 42 “Puma Unleashed”, and campaigned with Puma for four years, during which he was IRC National Champion, RCYC Sailor of the Year in 2012 and RCYC Club Champion.
In 2012 Hylton and his sailing partner, Johnny Cullum, purchased the GP42 “Vulcan". This team has won the IRC National Championships twice, successfully broken records in numerous offshore races, and took third place overall at the 2017 Cape 2 Rio, breaking the SA registered boat record. Hylton also sails on the Highland Fling race team in many overseas regattas.
Hylton has served on various committees, including chairing the Mykonos Offshore (SA’s largest offshore race) and the Hobie Tiger World Champs. He has served on committees for the Cape 2 Rio race and the RCYC as Rear Commodore Sailing. Currently he is a SA Sailing National Counsellor representing keelboat racing, and is the Chairman of IRC South Africa.