Stellenbosch, Western Cape

Stellenbosch is one of the most picturesque towns in South Africa. A mosaic of farms, old oak trees, and white-washed Cape Dutch dwellings, Stellenbosch is one of the best preserved towns from the era of the Dutch East India Company. Today, it's a university town with a vibrant feel and fantastic scenery. Foodies will love it here. Stellenbosch is home to some of South Africa's best restaurants as well as many sidewalk cafes. History buffs can take a walk back in time at the Village Museum, a group of four restored houses and gardens dating from 1709 to 1850. Rupert Museum displays important works by South African artists, and the Botanic Garden at the University of Stellenbosch is another top tourist attraction. In the surrounding area, nature buffs can hike and bike on the wilderness trails in the breathtaking Jonkershoek Nature Reserve.

Cape Town, Western Cape

One of the planet's most breathtaking cities, Cape Town is, by population, the second largest settlement in South Africa. Nature surrounds this multicultural city, which nuzzles between a rugged range of mountains and the sea. For a spectacular overview, hike to the peak of flat-topped Table Mountain, or glide up on the cableway. The hour-long hike up Lion's Head also provides panoramic city vistas. On Table Mountain's eastern slopes, the magnificent Kirstenbosch Botanical Gardens lie within a UNESCO World Heritage Site. Strolling along the waterfront boardwalk, visitors might see whales spouting from the harbor. Penguins waddle along the golden beaches in False Bay, while south of the city, Cape Point is home to abundant wildlife and diverse botanical wonders. One of Cape Town's top attractions is the Victoria and Alfred Waterfront. Reminiscent of Fisherman's Wharf in San Francisco, visitors come here to shop, dine, and enjoy the many entertainment venues, including Two Ocean's Aquarium. Camp's Bay, rimmed by beautiful boulder-flanked beaches, offers chic shops and cafes. At sunset, nature lovers stake a spot along spectacular Chapman's Peak Drive in a dusk ritual known as "sundowners" to watch the sun sink slowly into the sea.

Robben Island, Western Cape Robben Island, Western Cape

In Table Bay, World-Heritage-listed Robben Island is a haunting reminder of the horrors of apartheid. Nelson Mandela spent 18 years imprisoned in a tiny cell here along with other political dissidents and social misfits. Perhaps the best part about this experience is that ex-prisoners are usually the guides, sharing poignant first-hand accounts of the atrocities they endured. Tours to the island begin with multimedia exhibits in the museum at the Nelson Mandela Gateway at the Victoria and Alfred Waterfront. Sightseers then board boats to Robben Island, often braving rough swells on the 30-45-minute ride. Be sure to book early as the tours can fill up fast.