This trip was all over the place. That’s not a complaint — it’s an accurate description.
It started as a perfectly ordinary Saturday. Shawn had gone bicycle shopping that morning, which got the wheels turning on an idea I’d been sitting on: a bicycle for the overland build. Something to offload from Sarabi at a campsite, cover the last mile, explore spots you can’t reach with a vehicle. I’d been thinking about it for a while. That morning I went looking too.
Saturday 12 October — Bicycle Shopping
There’s a specific kind of Saturday energy that comes with going shopping for gear you don’t strictly need yet but can already picture using. We moved around the shops, looked at what was available, talked about builds and specifications and whether a fat tyre was worth the weight penalty. The kind of conversation that’s mostly hypothetical but feels very productive.
Later that Saturday evening, a message came in from Tim — an old school friend, based overseas. He was travelling to South Africa for a client presentation. Two days in Joburg for the work, then the rest of the week free to explore. He wanted to meet up.
At the same time, a call had come in about a client project that needed me in Joburg. I’d been thinking about a drive up anyway. It had been a while.
That settled it. Two reasons to be in Joburg at the same time, and an old friend coming in from overseas. You don’t wait for a third reason.
Sunday 13 October — Last Ride with Ndumiso
Before any of that could happen, there was Sunday morning.
Ndumiso was one of my regular riding buddies — the kind you fall into a rhythm with over weeks and months of the same roads at the same early hour, coffee before the ride, a debrief after. He was relocating back to Joburg. This Sunday was his last ride before the move.
You don’t know which ride is going to be the last one until it is. The ones that end up mattering are usually the ones that felt like any other until later.
Monday 14 October — Booking the Flights
The flights got booked on Monday afternoon. That’s the decision made concrete — the moment a plan stops being a plan and becomes an itinerary.
We picked Monte Casino as the base for Tim. The logic was simple: it gave him somewhere interesting to walk around before we flew back to Cape Town. Monte Casino is one of Joburg’s more distinctive landmarks — a Tuscan village built into a casino complex in Fourways, opened in 2001, designed by an American company and built at a cost of over a billion and a half rand. The fake sky painted on the ceiling transitions from light to dark across the interior, and the whole thing operates on the logic that if you’re going to be indoors, you might as well not feel like it. Restaurants, cinema, a theatre that can seat nearly 2,000 people. More than enough to keep Tim occupied while I sorted the client work.
Tuesday 15 October — Joburg, the Meetup
We touched down in Johannesburg Tuesday. The client project was the first priority.
By evening it was done, and that’s when the trip shifted into a different gear.
Tim and I met up. There’s a particular feeling when you reconnect with someone you went to school with and haven’t seen in years — the time compresses in one direction and expands in another. You pick up conversations that were put down a long time ago, and you also find out who you both became in the meantime. That combination doesn’t happen over a message. It needs a table and some time.
Monte Casino, Fourways
After dinner, we walked Monte Casino.
It’s a strange and committed piece of architecture. The Tuscan village concept is applied thoroughly — the cobbled piazza, the terracotta rooflines, the frescoes, the fountain, the whole theatrical treatment. It shouldn’t feel as comfortable as it does, but somehow the scale of the commitment to the concept ends up working in its favour. You’re not quite outdoors and not quite indoors, which in a Highveld October evening is not a bad place to be.
The Joburg Days
The middle of the week was Tim’s client work and, alongside that, Joburg doing what Joburg does. There’s a rhythm to Johannesburg that’s completely unlike Cape Town’s — faster, more deliberate, denser with traffic and consequence and the particular energy of a city that runs on its own terms. Tim had his presentations. I had my project. In between, we ate well and moved around the city.
No images from those days. Some of the best parts of a trip don’t get photographed.
Saturday 19 October — Cape Town, the Winelands, the Waterfront
We flew back to Cape Town.
For Tim, this was new territory. For me, Cape Town is the city I called home for many years, which puts you in an odd position as a host — you’re not quite a tourist but you’re not indifferent either. You’ve seen the mountain enough times that you’ve stopped noticing it, and then someone sees it for the first time next to you and you see it again.
We started the morning early.
The Stellenbosch Wine Route
The Stellenbosch wine route is one of those places that repays revisiting. The first time you drive it everything is new — the Cape Dutch homesteads, the oak-lined roads, the mountains closing in on either side of the valley, the estate after estate of vineyards spreading across the foothills. The second and third times, you start to have favourites. You know which side of the valley catches the morning light, and which estate has the better lunch.
In October, the vines are coming back. Spring in the Western Cape means new green growth on the trellises, the whole valley shaking itself awake after the winter. The mountains are clear and sharp. The light is good.
We drove in from Cape Town, took our time.
We picked a wine farm for lunch. That’s the right way to do the Stellenbosch wine route — pick one estate, sit down properly, don’t rush it. The wine is better that way than if you’re trying to hit six farms before three o’clock. A table, a menu, the mountain visible from wherever you’re sitting. Tim had been in boardrooms all week. This was the other side of the visit.
Cape Town CBD and the Waterfront
After the winelands we moved into the city.
The V&A Waterfront has a version of Cape Town that was specifically built for moments like this — warm afternoon, ocean smell, Table Mountain sitting behind everything, the harbour moving. If you’re showing someone Cape Town for the first time and you have one afternoon, you go to the Waterfront. It does the argument for you.
Tim had been looking forward to this. People who visit South Africa for work and never get south of OR Tambo miss the most obvious thing. Cape Town is not Joburg and it’s not supposed to be — the two cities have almost nothing in common except a country and a time zone.
For me, walking around a city you know well with someone who’s seeing it fresh is its own kind of experience. You stop noticing that the mountain is extraordinary until someone next to you can’t stop looking at it. Then you see it again — the flat top, the sheer face, the way it anchors the whole geography of the city around it.
How It All Fit
This trip was, in every sense, all over the place.
It started as a normal Saturday with bicycle shopping. It picked up a Joburg client project. An old school friend arrived from overseas with a calendar window and a client of his own. We ended up in hotels at Monte Casino for a few nights, saw Joburg by day and the casino by night, finished client work, flew south, showed an overseas visitor the Stellenbosch wine route and the Cape Town waterfront in an afternoon.
The bicycle didn’t get bought, in the end. Still on the list for the overland build. But that’s how these weeks go — you go looking for one thing and come back with something else entirely.
Tim flew home having seen both cities. Ndumiso relocated north. The client project got delivered.
The week wrote itself.