Chasing Wind And Wet Cobbles, 5 Days In Cape Town, South Africa

I came to Cape Town with a rough plan and a rental car, and the plan lasted until the first morning, when the light did something over the Atlantic that I was not expecting and I sat on a hill for an hour instead of going to breakfast. That set the tone for the whole five days.

What follows is the order I actually walked it in. Some days are city days, flat and easy on foot. Two of them need a car, or at least a willingness to spend money on taxis down the peninsula. I travelled on my own, which mostly meant I ate early, talked to a lot of waiters and tasting room hosts, and changed my mind often.

Wind runs this city, by the way. Check it before you commit to anything high up.

Day 1, Up the Hill and Into the Old City

I spent the first day getting my bearings from above and then slowly dropping back down into the city. A hill at first light, a long slow garden, the painted streets of Bo-Kaap and lunch at the top of them, then an old Dutch fort and coffee until my hands buzzed. Almost all of it walkable, except the first stop.

Signal Hill

First thing, before the cafes opened, I drove up with the city still grey underneath me. The road takes you all the way to the top, which feels a bit like cheating for a view this big. Table Mountain behind, the Atlantic in front, the whole bowl of streets below going from grey to gold while I sat on the bonnet. Paragliders were already laying their wings out on the slope by the time I left.

Everyone here will tell you the real event is sunset, and that you should be parked a good hour and a half before if you want a space. I came back later in the week and they were right.

One honest warning. The public toilets are in a genuinely bad state, flies and no water, so arrive sorted. Easy to lose an hour up here doing nothing at all. From the top I drifted back down into the city centre toward the gardens, a quarter of an hour by car.

The Company’s Garden

The oaks along Government Avenue were throwing long stripes of shade when I walked in, and within about four steps a squirrel had decided I was useful. They sell paper packs of nuts near the entrance for ten rand, which is the single best value transaction of my whole trip.

After the hill it was exactly the right pace. Benches everywhere, most of them shaded, Table Mountain sitting at the end of one path like a stage set. The rose garden was worth the detour. The vegetable garden, less so, it looked neglected and I kept thinking about how much food it could be making.

Easy to spend a couple of hours here without noticing, and there are two cafes inside if you want to stretch it further. I bought coffee and watched pigeons bully a toddler.

From the gardens I walked up Wale Street into Bo-Kaap, about ten minutes, uphill enough to feel it.

Iziko Bo-Kaap Museum

Rain had come through earlier and the cobbles were still dark and wet when I got to Wale Street, which made the greens and pinks and that one acid yellow look almost staged. The museum itself is small. Half an hour, maybe a little more if you read everything, and it is worth doing before you walk the streets rather than after.

Inside you get the part the photographs leave out. Modest rented houses built in the 1700s, enslaved people and exiles brought here from across the Indian Ocean, the colours arriving later as a sort of declaration once people could finally own the walls they lived behind.

It changed how I walked afterwards. These are homes, not exhibits, and people live their ordinary Tuesday behind those doors.

From the museum I wandered up through the lanes toward August Street, five steep minutes, for lunch at the top.

Bo-Kaap Kombuis

Lunch, and the climb up to it is no joke in the sun. The reward is a window with Table Mountain filling it, which is most of why people come.

Dinner here runs as a buffet and I found that out on arrival, so ask when you book, which you can do over WhatsApp. The starters were the real thing. Samoosas, patatas waras, and the daltjies, those little spinach and chickpea fritters, which I went back for twice. Lamb breyani and bobotie followed, hearty and generous, though the curries were milder than I wanted. An older gentleman who I think is the owner talked me through the whole menu before I had even sat down properly.

No beer or wine, so plan your drinking elsewhere. Give it an hour and a half. The view earns its keep even when a dish does not.

From there I walked back downhill into the city toward Castle Street, about twenty minutes and all of it in your favour.

Castle of Good Hope

A low pentagon of yellow walls at the edge of the Foreshore. Not a fairytale castle, more a working fort, built by the Dutch East India Company between 1666 and 1679 and still looking like it was made for soldiers rather than kings.

I arrived in that flat afternoon light and joined a guided tour that was already starting. Best thing I did here. The guide shut doors and killed the lights to show us how the rooms would actually have felt, and he was funny about it. There are several smaller museums inside, military and heritage and the governor’s house, plus whatever is set up in the courtyard that week.

It is not all cared for. The Dolphin Pond is grubby and some corners are visibly decaying. Entry closes around four, so do not leave this for late. Plan a couple of hours, more if you climb the walls for the mountain view.

Afterwards I drifted up Buitenkant Street, ten minutes on foot, for coffee.

Truth Coffee Roasting

By late afternoon my feet were finished and this was the plan all along. The inside is full steampunk, brass and iron and a roaster going in the middle of it, and there was a short queue for tables when I arrived. Takeaway got me in faster.

I had the black honey flat white, an Ethiopian and Honduran blend, smooth enough that I bought a bag of the beans on the way out. A barista talked me through the Involuntary Clairvoyance blend with the seriousness of a sommelier. Skip the desserts, mine was forgettable and I heard the same from the table next to me.

Thirty minutes if you are passing, an hour if you get a seat and start watching the room.

I walked back to my place as the office crowd emptied out of the centre and the light went orange on the upper windows. First day done, and I slept like a stone.

Day 2, The Island and the Mountain

Day two was built around a boat and a cable car, which means it was built around the weather. I ate first, then crossed to Robben Island, then let the afternoon drift along the water through the Waterfront and out to Sea Point before coming back for art in a grain silo. The mountain came last, on purpose.

Kloof Street House

Day two began with a slow first meal on Kloof Street, in a house full of small dark rooms and soft lamps. It feels like a speakeasy that got comfortable. Every room is different and I was moved to a better table without asking, which never happens.

The bread came with butter and a spread I could have eaten on its own. I had the South African bordkos, which is hearty and a little old fashioned in the best way, and then the malva pudding, which regulars here insist is the best in Cape Town. I am not going to argue with them.

Book ahead, it fills up and the bar seats are tight. Give it an hour and a bit, longer if you order dessert, which you will.

From Kloof Street it is a ten minute drive down to the Waterfront for the ferry, and you want to be early for that.

Robben Island Museum

Mid-morning, on the water, with Table Mountain getting smaller behind the boat. The crossing is part of it. Coming back the swell had picked up and the whole cabin was laughing nervously every few seconds.

On the island the tour splits in two. A bus loop with a guide who held the entire group quiet, then the prison itself, walked by a man who had been held here for seven years and came back to keep telling it. He was warm about it, which somehow made it land harder. I have rarely been so glad to be in a group of strangers all going quiet at the same moment.

Book online in advance. Take water and a snack, though there is a kiosk. Half a day gone, and worth every hour of it.

The ferry drops you back at the Waterfront, so you step off and you are already at the next stop.

V&A Waterfront

Straight off the boat and into the noise. Seals barking somewhere under the pontoons, a brass band playing near the amphitheatre, the Cape Wheel turning slowly against the mountain. For a shopping precinct it is a genuinely good place to walk, mostly because the harbour is still a working one and boats keep arriving.

I drifted for an hour with no purpose. Bought nothing. Watched a cruise boat load up, ate from the food court because the view from there toward Table Mountain is better than it has any right to be.

It is pricey, and some of it is just a mall with a view. But I was alone and it was the one place where I never thought about where my bag was, security is everywhere.

From the harbour edge I drove around the point to Sea Point, a ten minute run along the coast.

Sea Point Promenade

In that long late light, the promenade was full of people doing nothing in particular. Runners, prams, two men fishing off the wall, dogs very much in charge. The path is flat and paved the whole way, which makes it the easiest walk in the city.

The wind comes straight off the Atlantic here, even on a warm evening, and the water smacks the sea wall hard enough to throw spray onto the path in places.

I walked out and back without checking how far I had gone. That is the point of it.

Give it an hour, two if you keep stopping to look at the water. From Sea Point I drove back east toward the Waterfront silo for the museum, about fifteen minutes.

Zeitz MOCAA, in the old grain silo

The building got me before the art did. A grain silo on South Arm Road, carved out from the inside so the old concrete tubes curve up into a kind of atrium cathedral with light pouring down the middle. I stood in there much longer than I meant to.

Six floors, with a cafe and a terrace at the top and a rooftop view across the City Bowl to the mountain. Of the exhibitions, two floors genuinely moved me, in particular Gerard Sekoto’s journals sitting beside his paintings. Others I walked through quickly, and the basement school work was uneven. The lighting also throws a double shadow onto some of the perspex plaques, which makes them a nuisance to read.

Go on your birthday month with your ID and entry is free, which half of Cape Town seems to know. Easy to spend two hours.

From the silo I drove up Tafelberg Road, twenty minutes, to catch the cable car before the light went.

Table Mountain Aerial Cableway

Just before the sky started turning, which is the right time and also the busiest. I had bought a fast track ticket online a couple of hours ahead and walked straight on. People who did not were still queueing, and one couple told me they had waited well over four hours earlier in the week.

The cabin floor rotates as you rise, so you get the whole 360 without elbowing anyone. Less than ten minutes up. At the top there are paths of various lengths, a coffee kiosk, and a wind that will take your hat off the mountain and keep it.

Check the cableway app before you commit, it closes on wind without warning. Tickets stay valid the next day if it does.

I stayed until the city lights came on below me and rode down with everyone gone quiet. Then dinner somewhere close to bed, because I was done.

Day 3, Down the Peninsula

This is the car day. The road south out of Hout Bay is one of the most beautiful stretches of tarmac I have driven, and it leads to the windiest corner of the continent. Penguins in the middle, gardens at the end. Long day, very little walking between stops, a lot of looking out of windows.

Chapman’s Peak Drive

Day three started with the window down and almost no traffic. The road is cut into the cliff above the sea, a shelf of tarmac with rock on one side and a long blue drop on the other, and it bends enough that every corner gives you something new.

There are pull-offs along the way. Use them, because trying to look and drive at once here is a bad idea.

I stopped three times in not very many kilometres, once just to listen. No cars, no people, only the water working away at the rocks far below and a bird I could not identify.

Easy to turn a twenty minute drive into an hour, and you should. From the far end I carried on south toward the point, a little under an hour with the coast on my right the whole way.

Cape Point

After a slow start the wind at the end of the peninsula felt like a different country. It comes at you sideways and it does not stop, and every photograph I took has my hair across half of it.

The land runs out in cliffs here, high and sheer, with the old lighthouse sitting up on the ridge and a path climbing to it. I walked up slowly, stopped twice, mostly to brace against gusts. From the top the sea goes out in every direction and the horizon looks further away than it does anywhere else I have stood.

Take a jacket even in warm weather. I did not, and regretted it inside five minutes.

Easy to spend a couple of hours between the climb, the viewpoints and the walk back. From the point I drove around to the False Bay side toward Simon’s Town, about forty minutes of very pretty road.

Boulders Beach

You hear them before you see them. African penguins make a sound somewhere between a donkey and a squeaky hinge, and the smell arrives at about the same time.

The boardwalk takes you over the dunes to the main colony, hundreds of them standing about in the late morning like commuters waiting for something. Smaller than you expect, honestly. I had imagined something much grander and then fell completely for how unbothered they are. On the beach side you can scramble over the granite boulders and end up a metre from one. A dassie sat on a rock nearby supervising the whole operation.

Entry is through the national park and the queues get long, so come earlier than I did. An hour is plenty, two if you swim.

From Simon’s Town I drove north to Newlands, about forty minutes inland, with the afternoon still in good shape.

Kirstenbosch National Botanical Garden

In the late afternoon the mountain behind Kirstenbosch goes a deep blue-grey and the lawns empty out, and that is when I liked it most. I arrived with maybe two hours of light and lost all of it.

Paved paths, plenty of benches, everything labelled properly, which I appreciate more than I expected to. The protea garden was the one I kept circling back to, big woody flowers that look invented. The fragrance garden is worth slowing down in, and there is a useful plants section that explains what people actually did with all of this.

Entry is around 270 rand for an adult, which is not nothing, and it is still the best money I spent that day. If you land here on a Saturday there is a market with food and vintage stalls.

I stayed until the light went and drove back into town with the windows open and grass stuck to my shoes.

Day 4, Kalk Bay and the Constantia Farms

A fish lunch with waves under the window, then inland to the oldest vines in the country. I did three wine farms in one afternoon, which is one more than I would recommend to anyone who is driving. They sit close together in the Constantia valley, so the driving is easy, it is the tasting pours that add up.

Harbour House Kalk Bay

Day four opened with salt spray on the window. Harbour House sits right on the harbour wall in Kalk Bay, and at a window table the swell breaks close enough that you flinch the first time. Ask for one of those tables, or the small outside balcony if it is free.

Warm bread arrived unasked, with oil and vinegar. I had the line caught kingklip laksa, in a coconut broth with bok choy and broccolini, which was the best thing on the table. A friend of mine ordered fried hake and chips and the chips let the whole plate down, which in a fish restaurant feels like a strange thing to get wrong.

Two hours, longer if you start with oysters. There is a fire going on cold days.

From Kalk Bay I drove inland over the neck to Constantia, about thirty five minutes, and the landscape changes completely.

Jonkershuis Constantia

After lunch, which meant I should not have been hungry, I sat under the oaks at Jonkershuis and ordered scones anyway. They came warm with strawberry jam, cream and grated cheese on the side, which was new to me and now feels obviously correct.

The setting does a lot of the work. Whitewashed Cape Dutch buildings, vines running off down the slope, and a long path outside that people were walking dogs on. There is a glass roofed courtyard for when the weather turns, which it does.

The curries get talked about here, Malay style lamb and chicken with proper sambals, and the chicken liver parfait came up more than once at the next table. Service was quick and unfussy.

Easy to let an hour go. From the restaurant it is a two minute walk across the werf to the tasting room.

Groot Constantia

The oldest wine estate in the country, and you feel the years in the buildings more than in the glass. The tasting room has been recently redone, brighter and more modern than I expected, and they run cellar tours on the hour if you ask when you arrive.

Do the wine and chocolate pairing. The Sauvignon Blanc held up on its own and the Gouverneurs Reserve was the red I remembered later, but the chocolates are what turn the tasting into something you talk about afterwards. Not every pour landed for me, and I will say that out loud.

Parking is awkward. I ended up at the shop end and walked up, which is a pleasant few minutes alongside the vines with geese making their opinions known.

Give it an hour and a half with the tour. From here it is five minutes down to the end of Klein Constantia Road.

Klein Constantia Estate

In the flat gold of the later afternoon this was the one I did not want to leave. The estate sits right against the mountain and the tasting room is calm and quiet, elegant without anyone being snobbish about it.

I came for the Vin de Constance and it deserves the mythology, sweet and complex and lingering in a way that made me stop talking. The Blanc de Blancs zero dosage was the surprise, and the price of it would be comic back home. My host, Tenba, poured whites, reds and the dessert wine and never once rushed me.

You can choose a vintage and have the bottle sealed in front of you to take away, which I did, and which I then carried around South Africa like an egg. Book ahead by phone, especially if you want the longer cellar experience. An hour and a half.

From there it is ten minutes up Constantia Main Road for the last stop.

Beau Constantia

Just before the sky started turning, up on the high slope where the valley spreads out below you in rows. Of the three farms that day, this one had the view.

The tasting room is small and the tables sit close together, so you hear your neighbours’ whole holiday. I did not mind. I ordered the cheese platter, mainly for the jam preserve that came with it, and some oysters from Saldanha Bay dressed with lime and chilli. The bread arrived with a soft, faintly pink guava butter that I am still thinking about. There was a taco truck parked in the yard, which should not work here and completely does.

If you want the full tasting menu with the wine pairing, know that it is a serious spend and a long sit. I went lighter and stayed until the vines went grey.

Drove back into the city in the dark, windows down, slightly too much wine in me to feel like talking. Good day.

Day 5, Mountain Air and Cold Water

I wanted the last day to be physical and then lazy. A climb in the dark, a beach at midday, a long lunch above the water and the sun going down into the Atlantic. Everything on this day sits along one strip of coast, which made the final afternoon very easy to stretch out.

Lion’s Head, climbed before the light

Day five began in the dark with a head torch and a jumper I ended up tying round my waist within fifteen minutes. The trail spirals around the mountain, easy at first, then rock, then ladders and chains and metal staples bolted into the stone.

I had planned to do this on day one. Actually, scratch that, the wind made the decision for me and shoved it to the end of the trip, and I am glad, because by then I knew what I was looking at.

Fast people get up in under an hour. I took longer, stopped a lot, and reached the top as the sky behind Table Mountain went pink. Camps Bay, the Twelve Apostles, the whole coast laid out. Proper shoes and a windbreaker, no negotiating. By mid-morning you queue for the ladders.

Back down in about an hour, legs shaking. From the trailhead it is fifteen minutes down to Clifton.

Clifton 4th

Powder white sand, water the colour of a postcard, and cold. Properly cold. The kind of cold where you get in to your knees, make a noise, and reconsider your whole plan.

Fourth is the easiest of the Clifton beaches to reach, only a short flight of steps down, which after a mountain in the morning mattered. Vendors rent out loungers and umbrellas and they take cards, which still surprised me. There is almost no natural shade, so take one.

The odd thing here is the calm. The wind can be howling across the rest of the peninsula and this little bay sits still behind its boulders.

Park across the road where the guards watch the cars, and come early or late for a space. I lost most of the middle of the day here. From the sand I walked up to Victoria Road for lunch, five minutes.

The Bungalow by Kove Collection

Late lunch, on a terrace with the Twelve Apostles going up behind me and nothing but ocean in front. All white everything, cocktails, a crowd dressed better than I was in my salty beach clothes.

The sushi is the thing to order, genuinely fresh, and the roasted red pepper hummus with pita was better than it sounded. Their own house salad is enormous. Service was unhurried and friendly for me, though I had read enough warnings to arrive with low expectations.

Here is my honest take. You are paying for the setting more than the plate, and the prices know it. I still sat there for two hours with a glass of white and no regrets.

Book ahead and ask for outside, and be aware they may cap your table at two and a half hours. Private parking out front, which is rare along this stretch.

From Victoria Road it is five minutes south to Camps Bay.

Camps Bay Beach

I got here with maybe an hour of sun left, which is the only time I would choose. The Twelve Apostles turn pink behind you while the sun drops straight into the Atlantic, and the whole beach quietly turns to face it.

Wide, flat, clean, free to walk onto. At the southern end there is a tidal pool if you want a dip without fighting the surf, and the water here is just as icy as Clifton. People try to rent you chairs with varying degrees of honesty, so agree the price first.

Across the road the strip is all restaurants and cafes, so you can walk off the sand and straight into a drink.

I stayed until the sky went purple and the first lights came on along the road. Five days, ending barefoot on a beach. I could not think of a better way to close it out.

Five days is enough to feel the shape of Cape Town without pretending you have seen it. I left with a bag of coffee beans, sand in both shoes, a recipe for daltjies I am still trying to get right at home, and a long list of things I ran out of light for.

If you have been, tell me what you would swap out. I keep hearing I got the peninsula day wrong and should have gone the other way round the coast, and honestly, they might be right.