The Cape in Winter

The first time we visited the Western Cape, in January 2025, we fell for it pretty hard. So no surprise that since we moved to South Africa, we have made multiple trips back to the Mother City (which you can read about here and here).

On our first visit, we spent a few days between the city and the vineyards and left with that depressing feeling you get when a holiday destination is so good that you know real life is probably going to get in the way of ever seeing it again.

Except, somehow, real life did the opposite.

A year and a half later, I find myself living in South Africa, which means that a weekend in Cape Town is no longer a once-in-a-lifetime holiday. It can just be a weekend away. After the working week, we can get on a plane and be in the Western Cape for a couple of days before heading back to Johannesburg. I feel, in other words, a little like the cat who got the cream.

Although this past weekend was the first time we visited in winter. Winter in the Cape has a different reputation from winter in Johannesburg. While Joburg spends most of the season under relentlessly blue skies, the Western Cape gets the weather it has apparently been saving up all year: rain, wind, cloud. Our Joburg friends were therefore somewhat bemused by our decision to head south for the weekend. But there was a reason to go, and, conveniently, an excuse to make a weekend of it, so off we went.

And it turns out there is another version of the Cape that I hadn't seen the first time around.

Cape Town itself becomes moodier, quieter, and the seafront reminded me of a grey English seaside resort town passed its hey day. There was a vague sense that the city was waiting for summer to return. It isn't the Cape I fell in love with in January 2025. But it wasn't a bad time - and it was quite charming to see it without its Instagram filter.

Hotel room views over Bo Kaap.

There is, admittedly, less to do in the city in winter if your idea of a good time involves lying on a beach or hiking up a mountain. Table Mountain disappears into the cloud, the Atlantic looks actively hostile and even the most committed sea swimmer might think twice about getting into the water.

But Cape Town is not exactly short of ways to spend a weekend. If summer in the Cape is about being outside, winter seems to be about finding increasingly good reasons to stay inside. And on that front, Capetonians are very well served. Cape Town is, after all, a city that takes eating and drinking rather seriously. The winter weather simply gives you permission to enjoy all the incredible restaurant and bar options without feeling guilty about wasting a perfectly good sunny day.

Sheltering from the wind, the only way Cape Town knows.

From Cape Town, we headed out to Paarl for a couple of days. Like Stellenbosch, Paarl dates back to the early Dutch settlement of the Cape, with the town established in the late 17th century and its fortunes built largely around farming and wine. Its long Main Street is lined with old Cape Dutch, Georgian and Victorian buildings, with vineyards and mountains pressing in from either side.

Laborie Estate, Paarl.

But Paarl has a slightly different feel to Stellenbosch. Stellenbosch can sometimes feel as though it has been polished specifically for visitors; Paarl feels more like a place where people actually live. There are old manor houses and wine estates, but also ordinary residential streets, schools, shops and the slightly sleepy rhythm of a provincial town. Paarl's Main Road is unusually long, and old houses, farms and businesses still sit alongside one another.

We weren't there to do very much. Which, as it turns out, is an excellent way to spend a winter weekend in the Winelands. Without the summer crowds, there was no particular rush to get anywhere or squeeze in every possible wine farm before sunset. We spent a couple of lazy days driving (in an Uber) between vineyards, stopping for long lunches and tasting rooms, and allowing the weather to dictate the pace. Plus the cooler weather gives you a great excuse to drink copious amounts of red wine.

Alistair in Bacco Estate.

I suspect I'll always prefer the Cape in summer. There's something about the mountains, beaches and long evenings that makes it difficult to compete with. But winter has its own appeal. The weather forces you to slow down a little, and the Winelands in particular seem perfectly happy to oblige. A few grey days, a handful of good restaurants, some old buildings and enough red wine to see us through was more than enough for a weekend away. Even if Table Mountain did spend most of it hiding.

Notes from 26° South.