South Africa

South Africa is where my life as a digital nomad started. And it happened by accident. In January 2017, I got a WhatsApp message from my good buddy Jeremy that said, “Raymond, you should come hangout in Cape Town.” I immediate agreed; I was already working from home — and after getting a taste of traveling, for a few weeks at a time at the end of 2016 — I figured, why not?

After arriving, and spending 10 days in Cape Town, I cancelled my return flight… and spent the next 11 months traveling the world. And now — at the time of writing this guide (2019), I’m here again.

There’s a lot to see, do, and experience in South Africa. Before I get into the specific locations and activities, here’s some basic need-to-know info before you arrive.

Getting Around

Public transportation ain’t so great, so based on where you’re staying, you’ll want a car. I’ve relied on Avis, which allows you to book in advance and have a car ready your plane lands.

Travel time from airport to Cape Town is about an hour.

Alternatively, you can rely on Uber for getting to, from, and around Cape Town. But if you’re heading outside of Cape Town, to Stellenbosch or the Garden Route for example, I’d definitely recommend a car.


While I haven’t had any bad experiences, I know several people who’ve been mugged or pickpocketed.

Much like other places I’ve been to, here’s some general advice for keeping safe:

  • Avoid looking and dressing like a tourist

  • Always have a destination in mind (don’t look lost)

  • Never admit to traveling alone (even if you are)

  • Don’t flash your money, phone, etc.

  • When driving, be mindful of people reaching INTO your car and grabbing whatever is in your hand or lap (i.e., don’t keep your window all the way rolled down while using your phone)

One specific Cape Town specific hustle works like this:

  • Someone approaches you in a friendly way, and compliments your shoes

  • They’ll then compare their shoes to yours

  • As their leg is adjacent to yours, they’ll reach into your front pocket

I had this hustle attempted on me once, but I kept walking quickly during the shoe comparison — avoiding any chance for him to get close. Pickpockets in Cape Town are very good. No matter where you go, even in broad daylight, be mindful of your pockets — especially in the Central Business District (CBD).

Some other hustles to look out for:

  • Someone knocking on your door, claiming she’s running / in trouble. He or she will ask if they can come in, so you can protect them from safety. While it may seem like the kind thing to do, ask them to wait outside while you call the police. Chances are, they’ll run away.

  • I head about this one on the radio — a naked and attractive woman will flag you down while you’re driving. This hustle usually targets men, driving alone. Once the man stops, she’ll say she’s being raped and needs help… but once you stop, her accomplices will appear, catch the driver off guard, and rob them.

While this safety section might be long, don’t let it deter you from visiting South Africa. Crime can happen anywhere. Being mindful about it, and knowing what to expect in advance, is a good way to greatly decrease the chance of anything happening.


I had success using Tinder, Bumble, and OkCupid in South Africa. In general, the women I met had busy lifestyles; and were often spending their workdays working or attending classes. Because the economic situation in South Africa ain’t so great, people have to work and study hard.

Many of the women I dated told me it’s very difficult to find a man to date from South Africa. This is a good benefit if you’re here traveling. Often times, an invitation to dinner and being attentive to her was enough to be called a gentleman and, after taking the lead, a generous lover.

Cape Town

Cape Town is likely the place you’ll be spending most of your time. It’s a beautiful city with great weather and several spectacular restaurants and cafés. As I mentioned before, Uber is all you need to get around if you’re only staying in Cape Town.

The only caveat is if you’re staying in Camps Bay, a ritzy area in the hills. The reason why is because Camps Bay is about 15 minutes away from most restaurants and cafes. This makes calling Uber a 20-30 minute activity, every time you want to go out.

In no particular order, these are my recommendations for Cape Town.


Asoka is a Asian-inspired fusion restaurant off Kloof street. Reservations aren’t required on most nights, but I’d make them anyway to be safe. If you’re looking for a nice date night, this is it.

Loading Bay

I love coming to Loading Bay for breakfast and lunch. There isn’t anything on the menu that I didn’t like and the staff is great. There’s also an Aesop store on the second floor, if you’re looking to stock up on my recommended health products.

Solo Restaurant

The number one thing I love about Solo Restaurant is the quality of food. You can tell by the color of the eggs, avocado, and salmon that the food’s origin is top notch. What’s confusing about this place is the fact that it’s called a restaurant, but because the kitchen closes at 3:30pm, to me it’s more like a breakfast and lunch spot.

Botanical Bar

Located around the corner for Solo Restaurant, The Botanical Bar is a great place for coffee, drinks, and food. What’s unique about this place is the fact that they use lot of herbs for their custom-made cocktails. I also like the fact that they serve a wide assortment of healthy food during the day, buffet style. Another great date spot.


If I had to recommend only one place to visit outside of Cape Town, it would be Stellenbosch; a beautiful, vast wine country with farm-to-table restaurants, vineyards, and wine tours, only 1 hour away from the city.

You’ll definitely want to rent a car for this one, although I was told you can hire a driver for about $70 — which isn’t a bad deal. Personally, I prefer to enjoy the drive on my own.


Oudtshoorn is a desert-like area known for its ostrich farms. It’s a cool place to visit, if you happen to be in the area, as I was when driving the Garden Route. I only spent a few nights in Oudtshoorn, because I didn’t find much to see or do outside of learning, eating, and riding ostriches.

Bloukrans Bridge

Here’s where I unintentionally bungee jumped off a bridge. That is, it wasn’t planned. I was driving over the bridge, read a billboard that said “World’s Tallest Bungee Jump From a Bridge”, and couldn’t resist NOT doing it.

So, without overthinking it (because, you know, jumping off a bridge could be fatal), I turned around and took things one step at a time:

  • Parked the car

  • Bought a ticket

  • Suited up

  • Leaped off the bridge

Some of the things that helped me overcome the fear:

  • Telling myself I could die — and smiling (because if you’re going to die, you might as well smile)

  • Pretending I was bird — because if birds can leap off bridges, why can’t I?

Overall, it was a fun experience. And it (i.e., gravity) happened FAST! Going back up, however, was slow. It took a good 4-5 minutes before I was back on the bridge, which wasn’t the most-pleasant experience, considering I was hanging upside down most of the time.


Useful Services For South Africa

  • Uber - $2 off your first 3 rides

  • Avis