3 Days: With three days you can manage to see many of the city's major sights—including Company's Garden, Castle of Good Hope, District Six Museum, and the Bo-Kaap—on your own or with a tour. Weather permitting, try to also work in a Robben Island tour, which will take around 3½ hours, and lunch at one of the outdoor restaurants at the V&A Waterfront, where you can eat while watching working tugboats maneuver past sleek million-dollar yachts. The cable-car ride to the summit of Table Mountain is a must; go in the morning, and in the afternoon, drive out to Camps Bay, where you can kick off your shoes to stroll along the beach. To round out the evening, find a sophisticated sea-facing bar for a sundowner before going on to dinner. On another evening, discover the rhythm of Africa by heading to the Green Dolphin at the V&A Waterfront, where you can listen to terrific jazz. Or for a real taste of contemporary African music, go to Long Street's Mama Africa or Zulu Bar to hear pulsing marimba music or great local DJs.
5 or More Days: With at least five days, you can enjoy all the sights listed here as well as a trip to the Winelands in Constantia, Stellenbosch, Franschhoek, and Paarl. From the harbor you can take a cruise to Seal Island or, for a more adventurous activity, admire the sunset from the back of a horse at Noordhoek. Wend your way along the False Bay coast to Boulders Beach, in Table Mountain National Park, where you'll find African penguins in profusion. From here, follow the road to the Cape of Good Hope and Cape Point. You can take the steep walk to the point or ride the funicular. It looks as if this is where the Indian and Atlantic oceans meet—sometimes there is even a line of foam stretching out to sea—but of course it's not. (That happens at Cape Agulhas, on the Cape's southern coast.) For a late lunch make your way back to the pretty fishing village of Kalk Bay, where the streets are lined with antiques shops and there are plenty of excellent restaurants to relax in. However you spend your time, on your last night back in Cape Town have a drink at the Bascule bar at the Cape Grace (at the V&A Waterfront) and watch the gulls wheel overhead against Table Mountain. Chances are, you won't want to leave.