“The only man I envy is the man who has not yet been to Africa – for he has so much to look forward to.” -Richard Mullin
South Africa is unlike any other place I’ve ever traveled. Cape Town is somehow simultaneously wild and cosmopolitan. You can see great white sharks and penguins in the same day, and then hop on a Ferris wheel before grabbing some cocktails at the VA Waterfront . You can witness two oceans violently coming together at the Cape of Good Hope, and then visit a sleek winery to enjoy a 4-course meal. Steeped in history and full of vibrant people and landscapes – South Africa really has it all.
Full disclosure, we didn’t bring the kids along for this trip. At their ages, I wasn’t sure if I wanted to deal with two overnight flights and such a dramatic time change; however, we really want to do this trip again with the kids when they’re closer to high school aged. If you want to bring the kids along, I’ll do my best to add some kid-friendly itinerary items; however, South Africa is home to an amazing wine region as well. Perhaps your kids love wineries! I had to include them as an itinerary item since they are truly top-notch.
If you’re interested in safari options, please see Part II of this post for amazing animal photos and my suggestions.

Travel Notes
We were flying to South Africa from Chicago. When looking at flights and timetables, it seemed to make the most sense to fly overnight to Brazil and then overnight again to South Africa. It was a loooooong flight. We did splurge for better seats on the flight so that we could lay down and get some sleep. We had nearly an 8 hour layover in Brazil, but couldn’t leave the airport since we didn’t have the right vaccines. With everything I read about traffic in São Paulo, I’m not sure we really could have done much in the city anyway. So download a lot of books or Netflix and podcast favorites! When I lay out the itinerary with “Day 1” just know that means after several travel days, depending on your hometown location.
We did rent a car in Cape Town. My hubby did nearly all of the driving, but it didn’t seem that bad. Roads are clearly marked, the highway is efficient, and sometimes you see some baboons (yes, seriously). South Africans drive on the left side of the road and all of the road signs are in English. When we went out in the evenings, we just used Uber so we didn’t have to deal with parking. And we wanted to enjoy allllll the local wines without driving back to the hotel!
This might seem obvious, but remember that the seasons are switched in the southern hemisphere. If you’re from the USA, Canada or Europe remember that your summer is their winter. We visited in June and were quite comfortable in a fleece. We also didn’t encounter many mosquitoes that time of year.




Day 1
- We stayed at the Cape Heritage Hotel which had on-site parking, complementary coffee, a free breakfast buffet, wifi, and a great location. The staff was really friendly and knowledgeable about the area. The rooms were also really lovely and crammed with interesting art and furniture.
- We’ll pretend that you’re perky and totally jet lag free! Let’s shake off the sleepies with a little hike. We’re headed to Table Mountain this morning. This flat-topped mountain dominates the skyline of Cape Town. You could really spend all day here if you wanted to hike the various trails in Table Mountain Nature Reserve. It’s about a 15 minute drive from the hotel to the most popular hiking trails. There’s also a cable car to the top if you want to be a cheater. The cable car website is extremely detailed and helpful. Several of the nature parks in South Africa have fees, and many do NOT take cash. They range from about 200R ($10 USD) to 400R ($20USD) per person.
- After a vigorous hike and great views, we’re headed to The Old Biscuit Mill for some lunch and shopping. It’s about a 20 minute drive from Table Mountain or you could certainly Uber. The Old Biscuit Mill is an awesome indoor/outdoor market. If you’ve read any of my other posts, you’ll know that I’m obsessed with markets. You get a little bit of everything under one roof! This was an actual biscuit mill until 1946, and then it was converted into a huge multi-shop bazaar full of restaurants and local artisans.
- We’ll end our day at the VA Waterfront, which is about 5 minutes from the market. As a Chicago native, this seemed a lot like Navy Pier to me. There are plenty of bars, restaurants, modern shopping, a Ferris Wheel, street performers, and a fun vibe. Try a Striped Horse beer!
- Nestled in the VA Waterfront is the restaurant Karibu. If you’re feeling adventurous and want to eat some ostrich, venison, and springbok, this is your place! Order everything! They also have plenty of beef, chicken and seafood if adventurous meals aren’t your thang. I’d also highly suggest eating chakalaka. Not only is it super fun to say, but it’s delicious! It’s like baked beans with turmeric and chunks of veggies.





Day 2
- I hope you’re not scared of the ocean…we’re going cage diving with sharks! If you just peed your pants a little at the thought, let me ease your mind. First of all, I barely swim. Seriously. I’m a doggy-paddle girl at best. But where else are you going to potentially see a great white shark? You have to trust me and DO IT. There are several tour companies with good reputations in the area. We went to False Bay and Seal Island with Apex, which left before the sun was up…so set that alarm clock. I’ve heard that more sharks are heading toward Gansbaai, so you may want to check out that trip too. I liked Apex because it was a maximum of 12 people on board, they gave you all of your gear (wetsuits, goggles, etc.), towels, snacks, and seemed ethical. If you do the False Bay tour, it’s about a 40 minute drive to Simon’s Town. Gansbaai is quite a bit further at 3 hours from Cape Town. Bring a waterproof camera or GoPro to capture the moment!
- On the way back from your amazing shark adventure, drive along the coast to the little town of Fish Hoek and explore. There’s an awesome seafood restaurant there called Live Bait with ridiculous sea views and even better food. They also have seals that like to hang out in the marina there.
- You’re probably pretty tired from your early morning, so I suggest grabbing some dinner near the hotel and heading to Long Street for a drink before passing out. Long Street is famous for bars and nightlife, so check it out if you feel up to it. It’s just a two block walk from the hotel.








Day 3
- Yesterday was full of danger and adventure, so today we do some chill hiking and see one of my favorite animals – penguins!
- At your leisure, drive as far south as possible to the Cape of Good Hope. It’s a little over an hour’s drive, but beautiful all the way down. This was originally called the Cape of Storms in the 1400s due to the clashing of the Indian Ocean and the cold arctic waters. All of the hikes here well marked and pretty easy. There are little beaches to explore, animals everywhere, and the views cannot even be described. Explore, contemplate life, stare out into the abyss of the sea, and enjoy the salty air. We also encountered wild baboons and ostrich here, so definitely bring your camera!
- When you’ve had your fair share of the Cape, drive 30 minutes north back to Simon’s Town. This is one of my trip favorites – Boulder’s Beach! Home to thousands of wild penguins! Children would love this place. There are several beaches and boardwalks where you can view the adorable tuxedo-ed birds up close. There are only 2000 of these African penguins left, so see them while you’re able.
- Wander the local beach, enjoy Simon’s Town, and find some dinner where you can watch the sun set.









Day 4
- It’s time to learn about some South African history. This morning, we’re headed to Robben Island to learn about Nelson Mandela who was a South African anti-apartheid activist and politician who served as the first president of South Africa from 1994 to 1999. He was infamously incarcerated at Robben Island Prison from 1964 until 1982. Tours are offered daily at 9AM, 11AM, and 1PM. You’ll take a ferry to the island from the VA Waterfront.
- Grab some lunch at the Time Out Market after your tour. The market’s 13 kitchens play host to some of the most innovative chefs and restaurateurs from across Cape Town.
- We’ve been on the east side of the peninsula quite a bit, so today we’re taking a drive down the west coast. There’s a famous driving route called Chapman’s Peak. This will take you along amazing coastal views from Hout Bay to Noordhoek. It’s a 9 kilometer drive with 114 twists and turns as you wind your way down the coast. There is a toll, but it’s nominal – less than $5USD for a car. Check the website before you go as the road can close due to bad weather.


Day 5
- It’s time to visit WINE COUNTRY! South Africa has some amazing vineyards that will rival anything I’ve had from Napa Valley. Plus, these wines are a lot cheaper than their American counterparts. The main wine region is Stellenbosch which is less than an hour’s drive from Cape Town.
- You could stop at the Kirstenbosch National Botanical Garden on the way. We visited during Africa’s winter season, so we didn’t see it, but I’ve heard it’s really beautiful.
- Wine country definitely has a peak season and a slow season. When we visited in June, it was pretty empty…but the wine was just as amazing. We stayed at the gorgeous Clouds Estate, which is a 5-star hotel. June is “low season” so it cost about $215 per night. However, in “peak season” (December and January) it’s nearly $700 per night.
- I would advise you to hire a driver for some wine tours. Our guide was not only knowledgeable about the wine region, but was also eager to chat about his experience growing up in South Africa during Apartheid which was quite eye-opening.
- Definitely visit Muratie and Fairview wineries today! They’re really close geographically and some of our favorite wines. Muratie is one of the most enchanting vineyards I’ve ever seen. It’s a lovely old building covered in cobwebs. You’ve never seen anything like it. Fairview is a totally different vibe, as it’s covered in goats! You’ll get some amazing cheese with your wine tasting here. They also have a great restaurant onsite for lunch.
- After drinking all day, I’d suggest a dip in the hotel pool or a stroll around downtown Stellenbosch. There are tons of cool shops and restaurants. We bought some wooden giraffes that now grace our dining room.






Day 6
- Today is pretty much the same as yesterday, but with new wineries to explore!
- Check out Delheim and Kanonkop today! Both have lovely tasting rooms and even better wines. Be sure to check out Pinotage while you’re in South Africa. It’s a red wine grape that’s a cross between pinot noir and cinsaut – so think black fruits, rich, and spicy. You can buy them in the US for under $20 per bottle, and they’re actually really tasty.
- If you’re tired of wine, try a local brewery! The Franschhoek Beer Co. is a great palate cleanser with a fun vibe.
- There are also other wine regions in the area to check out like Paarl and Franschhoek. Just google “vineyard” or “winery” in this area, and you’re sure to get a lot of results.
- If you want a fancy dinner, try the Delaire Graff Restaurant.






Day 7
- You traveled all the way to Africa, so you should really do a safari! We flew up to Johannesburg and then caught a tiny flight on CemAir to Hoedspruit for our safari. The airport in Johannesburg is…special. it’s a huge airport with practically no signage and the electricity kept cutting out. We made it in one piece, but it was the craziest airport experience.
- Read all about safari life at Garonga on my Part II post!



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