Stellenbosch is home to South Africa’s oldest wine route, with more than 100 cellar-door experiences across its various sub-routes. Afternoon: Head for the vineyardsYou can’t spend a weekend in Stellenbosch without giving its wine country some attention. The Stellenbosch Wine Route is the oldest in South Africa and is divided into five sub-routes: Greater Simonsberg, Stellenbosch Berg, Helderberg, Stellenbosch Valley and Bottelary Hills. The point of a Stellenbosch weekend is not to collect tasting rooms like stamps. The estate’s vineyards sit at different elevations and orientations, giving visitors a chance to see how varied the Stellenbosch landscape can be.