2 Week South Africa Itinerary: Bucket List Trip for Wine, Safaris and More

If South Africa isn’t on your bucket list, it should be. The country is unlike any other destination, with wildlife, beaches, cultural attractions, and wine tasting all at your fingertips. If you’re hoping to see the Big Five in the wild, sip Pinotage, and visit the stunning city of Cape Town, South Africa is for you.

This itinerary is structured as a 14-day trip, however, you can easily adjust the time frame to suit your budget and preferred length of travel. You can also use Winetraveler’s itinerary builder to design your own. Follow the below tips and itinerary to make the most out of your trip.


Getting To South Africa & Travel Logistics

South Africa is on the other side of the world, so it will take some time to arrive. United offers nonstop flights from Newark (EWR) to Cape Town (CPT) seasonally. Delta flies from Atlanta (ATL) nonstop to Cape Town, too. These flights typically take just over 14 hours heading over.

United also flies from Newark to Johannesburg (JNB) nonstop, as does Delta from Atlanta. Note that you can also arrive in South Africa via Europe and the Middle East, stopping in places such as London, Dubai, or Doha. You can browse flights in and out of any of these destinations, and get notified when flight deals arise. Many travelers opt for flight connections to JNB or CPT for more departure airport optionality.

RELATED: 11 Proven Methods For Getting Cheaper Flight Tickets

Once you’re in Cape Town, car rental is easy as everything is in English. But remember, in South Africa, you drive on the opposite side of the road.

Even if you don’t want to spend a significant amount of time in Johannesburg, the city is an ideal gateway to Krueger National Park for a safari. From Johannesburg (or Cape Town), the easiest option is to fly to Hoedspruit, where your safari lodge can send a car or van to collect you. 

For exploring the West Cape and the Cape Peninsula, Cape Town is the obvious choice for a base.

14 Day South Africa Bucket List Itinerary
This 2 week South Africa itinerary will help you explore destinations like Johannesburg, Kruger National Park, Cape Town, and the wine region of Stellenbosch.

Recommended Hotels in South Africa

While South Africa has lodging options for every budget, we recommend making your trip a once-in-a-lifetime experience by splurging on accommodation. Safari options range from budget to luxe, but some of the best are the Singita Lodges. You can browse a range of luxury lodges right here. They’ll cater to your every need, offering guests the opulence of a five-star resort, but also incorporate the beauty and peace of the surrounding nature and game reserves. These are truly one-of-a-kind experiences you can’t find anywhere else in the world.

In Cape Town, the famous Silo Hotel overlooks the waterfront — and this grain silo-turned-hotel has some of the most beautiful bathtubs the Winetraveler staff has ever seen! Another option is the Mount Nelson hotel, a Belmond Hotel, which offers charming cottage-style accommodation.

If you choose to stay a night or two in Johannesburg, The Four Seasons Westcliff is set on a hill with breathing views of the city and beyond. If you’d rather spend the night in wine country, some of the best wineries also have accommodation, like the stunning Delaire Graff Estate, where you can relax and wine taste in the lap of luxury.

READ: African Safari Planning Guide: 20 Tips To Prepare and Book a Safari

2 Week South Africa Itinerary: Johannesburg Markets
Markets in various neighborhoods in Johannesburg are vibrant and provide a great glimpse into the local cuisine and culture.

Days 1 – 3: Start in Johannesburg

Johannesburg is often overlooked, but if you’re hoping to catch a glimpse of South Africa’s complicated past, spend a little time in the country’s capital city. This city was once considered to be a bit too hectic for a travel destination, with safety concerns often pushing tourists to skip it and head for Cape Town. This is no longer the case. In recent years, Johannesburg has become South Africa’s most affluent city, with many of its older structures being renovated and turned into vibrant marketplaces and art galleries. It’s also an ideal city to visit to sample a wide variety of African cuisine.

Visit the Neighborgoods Market (located in the Braamfontein neighborhood) on weekends for live music and some of the best examples of food across the city. Step back in time and visit the Apartheid Museum, one of the most interesting and unique cultural centers for understanding South Africa’s history. Wander the Maboneng district to see local street art and pop into any number of the innovative cafes and restaurants for a bite. It’s also a great district to shop and experience some unique takes on nightlife.

For first-timers and one of the best ways to experience both Johannesburg and Soweto, take a full-day guided tour with our local friend Solly. The day trip is perfect for those who don’t know where to start and don’t want to have to worry about the logistics of navigating South Africa’s largest city.

Johannesburg is also home to the Gold Reef City theme park. This is a family-friendly place that offers a glimpse into the 1886 gold rush, while also providing unique amusement park rides like their rollercoaster which takes you through an abandoned gold mine. There’s also a casino and over 18 variations of rollercoasters to try.

About 50 kilometers north of Johannesburg, you’ll find what’s come to be known as the “Cradle of Humankind.” It was designated a UNESCO World Heritage Site back in 1999. Here, you’ll find limestone caves that are believed to have once housed some of the earliest humans, with archeological evidence going back over 3.5 million years. Tours are offered for a deeper dive, and include everything from boat rides to interactive museum exhibits and tours of the Sterkfontein Caves themselves.

2 Week South Africa Itinerary: Kruger National Park Safari
Lions spotted in Kruger National Park. Many luxury lodges in the park offer all-inclusive accommodation and safari excursions.

Days 4 – 6: See the Big Five in Kruger National Park

If you’re hoping to view lions, leopards, rhinos, elephants, and buffalos in their natural habitat, do a safari in Kruger National Park. Although you can see wildlife year-round, peak safari time is usually between July and October, dry season. Because there’s less rain, animals often congregate around watering holes, making them easier to spot.

Luxury, private lodges dot the perimeter of the park, and one of the most convenient ways to experience Kruger is to spend a few days at one of these lodges. Direct flights run daily out of Johannesburg, and last just about 90 minutes. Once you arrive at the park, lodge staff will meet you on the landing strip and take you right to your suite. Most Kruger lodges are all-inclusive experiences, complete with accommodation, safari trips, transfer, and transport services. For one of the ultimate luxury safari experiences, we recommend Lion Sands River Lodge

If budget is a concern, self-driving is also an option. You can expect a 6-hour ride from Johannesburg to the park along a well-maintained road. There are plenty of gas stations and opportunities to safely stop, rest and refuel. If you don’t want to spend the night in the park, full-day private safaris are also offered.

Cape Town South Africa Itinerary 14 Days
Aerial perspective of the city of Cape Town.

Days 7 – 9: Cape Town for Culture and Nature

Cape Town isn’t just one of the most beautiful cities in South Africa. It may just be one of the most picturesque cities in the world! Its waterfront location with prime access to mountains, beaches, vineyards, and beyond makes it one of the best bases to explore the Cape Peninsula.

Once there, make sure to see all the main attractions. Ride around in one of the red tourist buses, hike to the top of Table Mountain, see the colors of the Bo-Kapp neighborhood, and wander the V&A Waterfront

Nearby, pay a visit Robben Island to see where Nelson Mandela was once imprisoned. Beach lovers should hit the white sands of Camps Bay. And don’t miss the gorgeous Kirstenbosch National Botanical Garden, which has over 7,000 different types of plants, as well as a unique tree canopy walk.

READ: 10 Top Things To Do When Visiting Cape Town South Africa

Don’t forget about the African penguins

Just a short drive from Cape Town, you can see another very special kind of wildlife: African penguins. Boulder Beach is one of the best places to view them. Stroll around wooden boardwalks and between giant boulders to see these adorable animals go about their daily life. Watch and giggle as you observe the penguins eat, swim, waddle around, and hang out with their penguin friends.

If you want to see all of Cape Town’s highlights and experience some of the most scenic drives (and visit the penguins), this private tour is perfect for couples.

The Stellenbosch wine region is now considered a premier wine tourism destination. It's best known for its Pinotage grape variety.
The Stellenbosch wine region is now considered a premier wine tourism destination. It’s best known for its Pinotage grape variety.

Days 10 – 14: Sip Pinotage in Stellenbosch

South Africa’s coastal wine region is one of the best if you’re into wine tourism. The area includes world-renown subregions such as Franschhoek, Paarl, and of course, Winetraveler’s favorite, Stellenbosch. Spend the last 4 days of your trip exploring these 3 regions, and stay at the upscale Devonvale Golf & Wine Estate.

Stellenbosch is an easy drive from Cape Town. It’s close enough for a day trip, but also ideal for those wanting to escape the city and relax in the tranquil hills of the region for a few nights. With over 200 wineries, you’ll have plenty to choose from when it comes to wine tasting. And, you can even do a wine safari or wine picnic at wineries such as Waterford Wine Estate or Warwick Wine Estate. One of our favorite ways to see Stellenbosch is by bicycle hopping winery to winery.

For more Stellenbosch inspiration, make sure to read our guide to some of the best Stellenbosch wineries to visit.

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