Travel about 30 minutes from the Cape Town Airport or 45 minutes from the City Centre to Stellenbosch, founded in the late 17th century by the Dutch colony's first governor Simon van del Stel, who named the settlement after himself. The first grapes were planted not long after. Today, surrounded by vineyards, it is a bastion of Africaans or Boer ("Dutch" for farmer) culture. Expect to hear more Afrikaans than English here. Soak up the atmosphere by making the Stellenbosch Hotel, itself a historic building, your base.
Stroll at your leisure through the charming village or get your bearings on a free walking tour around the 300+-year-old town. No reservations required. Just show up at the green umbrella at The Braak next to St. Mary's old church off Bloom Street at 10 am or 1 pm. Tours take about 90 minutes and are tip-based.
Take a closer look at the distinctive Cape Dutch architecture in the four restored homes and gardens that make up the Stellenbosh Village Museum. Local women in period costumes at each house lend a personal touch to history. The homes - dating from the 17th to 19th century - are close to one another, but allow a couple of hours for full flavor.
Slip into the tranquility of a mini-Kirstenbosch in the botanical garden Stellenbosch University maintains in the center of town. The perfect place to relax any time of year, the garden has a well-marked plant collection, bonsai section, lily pond and the Katjiepiering Restaurant where you can stop for tea and cake or a tasty lunch. The university, founded by a wealthy Boer farmer, is a public research university where the world's first successful penis transplantation was performed in 2014.
Spend the afternoon and lunch at Spier Wine Farm about an 11-minute drive down R310 from the village. Spier offers Segway tours of the vineyards, eagle viewing, a craft market, wine tastings and the choice of three restaurants and a pub. It also has accommodations for staying over.
Barhop the night away in this university town. Good spots to check out include the Aandklas bar, the dance floor of the upscale Nu'Bar and the DJs and alternative live music at Die Mystic Boer. If your tastes are more cultural, check out live theater in the village and on campus or take an evening ghost tour.