Established in 1685 by the then governor of the Cape, Simon van der Stel, this wine estate's globally renowned dessert vintages were enjoyed by Napoleon, Bismarck, and Jane Austen. Vine-killing disease put paid to the farm right up until 1975, when the vineyards were replanted for the first time in over a century. Since the opening up of tourism in Cape Town after the dawn of democracy in 1994, Groot Constantia has become an essential stop for a mix of history and wine-tasting. Besides grappling with the wines, there's a small on-site museum depicting the manor house's history. The original Cape Dutch house contains late 18th-century Cape furniture, making it insightful for a crash course in period architecture and interior design. There's also a wine museum housed in the old cellars.

You can dine here, too. Jonkershuis (+27 21 794 6255) is a bistro adjacent the original homestead with cozy interiors and courtyard tables beneath the oaks for fine weather days; the menu reflects local Cape Malay influence. Locals tend to linger at Simon's (+27 21 794 1143), Groot Constantia's popular choice for alfresco dining, with a more French-leaning menu.

This historic estate is an ideal place to start explorations of the city's oldest and most accessible vineyards. While comprising just eight wineries (other famous stops include Klein Constantia, Buitenverwachting, Uitsig, and Steenberg, with Eagles Nest offering superlative boutique vintages), the area is dense with character and history. The big estates feature Cape Dutch homesteads, oak trees, and vast swaths of vineyards, and they're only about 30 minutes from town, ideal if you don't have time to venture into the surrounding Winelands.