Great Itineraries: South Africa in Two Weeks

Depending on where your inbound flight lands, you can begin or end with Cape Town. Most long-haul flights allow you to start and end wherever you wish.

4 Days: Cape Town and Environs

In four days, you can enjoy Cape Town's attractions at a leisurely pace. Take two days to explore the city’s outdoor spaces and fabulous markets. Live music and laid-back days are enjoyed in most open spaces in summer—including the almost legendary Kirstenbosch National Botanical Gardens on the backside of Table Mountain, and the Company’s Garden in the city center—surrounded by museums and the anti-apartheid political landmark, St. George’s Cathedral.

On Day 3, get an early start and take a day-pack hike, allowing you to take in the scenery of Table Mountain and recharge, far away from a car. If you don't do Table Mountain, Lions Head is a good option if time is tight, because both offer spectacular views. Lunch could be a leisurely picnic on the lawn of the Roundhouse in the Glen, right below Lions Head, overlooking Camps Bay. Then try a restaurant along the Mouille Point promenade for dinner. Use Day 4 to make a full loop of the Cape Peninsula, heading out of town through Hout Bay, over Chapman’s Peak Drive (one of the world’s most spectacular), then making for Simon's Town for a walk along the boardwalk among the penguins at Boulders Beach. Be sure to make it to Cape Point for a walk around Cape Peninsula National Park.

Logistics: If you don't want to drive yourself around Cape Town, then tours can get you to all the same places. For a longer stay, pick a more relaxing location for your hotel than the V&A Waterfront. There are plenty of inviting guesthouses and B&Bs.

3 Days: The Garden Route via the Cape Winelands

Heading out from Cape Town on Day 5 you'll have plenty of time to linger over culinary tastings in Stellenbosch, dine on gourmet French food in Franschhoek, and stroll alongside Paarl's mix of Cape Dutch, Edwardian, Victorian, and art deco architecture lining the main street. With so many excellent guesthouses to choose from, part of the fun is deciding which fantasy accommodation suits you best (and in which town)—from tranquil lakeside to mountain or historic main street cottages in Stellenbosch, Paarl, or Franschhoek.

Begin Day 6 with a drive to Hermanus for lunch, where you can watch whales from the shore—or if your sea legs are up to it, try a little shark-cage diving around the corner in Gansbaai. Spend the night in remarkable accommodation at the scenic Grootbos Private Nature Reserve.

Next day, head for Africa’s southernmost point, Cape Agulhas, also called the Cape of Storms, with its own standout vineyards and shipwreck history. Five minutes around the corner from the rocks is Stilbaai, with 30 km (19 miles) of empty sandy beaches, gentle surf, and seafood. Spend the night in Knysna or Plettenberg Bay. The former is packed with history, standout golf courses, forest, and water sports; the latter has some of the best swimming beaches in the country, framed by mountain ranges and the ocean.

Logistics: Rent a car in Cape Town for the remainder of your trip. You could accomplish everything with guided tours, but it's nicer to go at your own pace.

5 Days: Eastern Cape Safari Parks

An early start from your accommodation will see you cruise past the turnoff to the surfing mecca of Jeffreys Bay as you make your way to the outskirts of Port Elizabeth. The remaining time is for winding down in sublime surroundings. Spend them between the Addo National Elephant Park, where you will overnight and where you’re bound to see some of the best elephant activity on offer, and Samara Game Reserve, a little more than two hours inland outside the beautiful historic Karoo town of Graaff-Reinet. Samara is a remarkable reserve that has reclaimed old farming land and been restocked with indigenous game since it was purchased. It has a standout cheetah-monitoring program and employs locals. The privacy and accommodation are as good as it gets (and don’t forget the resident rhino population).

Logistics: Spend two nights in Gorah Elephant Camp in Addo, and two more nights in Samara Game Reserve.

2 Days: Johannesburg

After your Eastern Cape safari, you'll be relaxed and ready to head to Johannesburg, Africa’s shopping mecca, for two final days of exploring. Visit the Maboneng precinct, see the city’s exciting rejuvenation, watch some theater, and take a quad bike through Soweto—with both days accompanied by excellent food. It's a fine way to complete a fantastic trip to South Africa.

Logistics: It's a two-hour drive back to Port Elizabeth, where you board a flight to Johannesburg for two final nights. There, you can see everything on guided tours.