3 Day Cape Town WINTER Itinerary 

Last Updated on April 6, 2024 by thecapetownblog

If you’re planning on visiting Cape Town during the winter, you might be wondering how to fill your days without all of that glorious warm weather and sunset that we get during the summer. 

I’ve been there – the first time a friend came out to visit me, she came in July, which is one of the coldest and wettest months! And yet, we had no problem filling two weeks together because there’s just so much to do in this city, even during the winter months. 

Lots of people who visit Cape Town in winter combine a trip to the city with a visit to the Kruger, since this is prime time to go on safari! Most other itineraries you’ll come across are also designed for the summertime, so I wanted to create a short and sweet itinerary to help you experience the best of the city, even when it’s too cold to go to the beach. Let’s get into it! 

Arrival + Getting Around

I recommend renting a car in Cape Town, because public transport here is limited, so it gives you way more freedom to get around. Since I don’t own a car here, I use DiscoverCars to find affordable rentals from reputable companies for when friends come to visit. They even gave me a free upgrade last time, which was pretty sweet! 

However, if you don’t want to rent a car, you can always use Uber to get around the city, and then book tours to explore more of the Cape Peninsula. I’ll include some recommendations as I go! 

Day 1 – Get to Know Cape Town

Morning – Go up Table Mountain 

Going up Table Mountain is a MUST – it’s Cape Town’s most iconic attraction, after all! The views from up here are insane, and you can see for miles in every direction. I’ve been up to the top quite a few times and I’m always totally blown away. 

You can hike to the top of the mountain but with this itinerary, time is of the essence, and the trails can be slippery during the winter. So I suggest that you take all the cardio out of it and ride the cable car to the top instead! 

A return ticket costs R420 in the morning, and if you’re going during the winter, there’s no need to book them in advance. Ticket queues can be long during the summer, but when I went up the mountain during the winter, we arrived and went straight up! 

At the top, you can join one of the free guided walks that leave from the Twelve Apostles Terrace every hour, from 9 am until 3 pm. Or, on a clear day, you can hike to Maclear’s Beacon, which should take you about an hour. Personally, I tend to walk around for a bit, enjoy the views, and then head to the bar for a beer. (What? It’s five o’clock somewhere!)

Afternoon – Food tour 

I love this food tour because it combines two must-do Cape Town activities: strolling around Bo Kaap’s colourful houses, and eating and drinking as much as possible. In fact, it also takes you to De Waterkant, which isn’t as famous as Bo Kaap but is also home to lots of pretty, pastel-coloured cottages. It also happens to be where I used to live! 

You kick off at the Bo Kaap deli, which is pretty much the best place in Cape Town to try Cape Malay treats, and your guide will take you to other foodie hotspots like Marco’s African Place, the Charles, and the Fireman’s Arms to try some South African classics. I think that this is a great way to learn about just how many different cultures have shaped Cape Town’s food scene. 

The tour includes tons of food and alcohol, so it’s right up my alley, but it’s also such a great way to get acquainted with Cape Town’s layout and history. Plus, my former housemate, Marianne, is one of the guides on this food tour, and she’s an amazing person, so you’re definitely in for a treat if you’re in her group! 

This tour kicks off at 12 pm, and costs R1,985 per person, which includes all of your food. You also get free cancellation up to 24 hours beforehand. It doesn’t run on Mondays, so if your first day in Cape Town happens to fall on a Monday, I’ve got you covered with an alternative below. 

Monday alternative – Lunch in Camps Bay and free walking tour of Bo Kaap 

Okay, so as much as I think the food tour is the best way to spend your first afternoon in Cape Town, it doesn’t run on Mondays. But don’t despair because after Table Mountain, you can always go for lunch in Camps Bay instead and soak up those beautiful beach views, even if it’s not warm enough to sunbathe. In my opinion, Chinchilla offers the best views, but for something cheaper I’d recommend heading to Tiger’s Milk and requesting a table upstairs. 

Then, you can turn up at Parliament Street at 4 pm and join a free walking tour of Bo Kaap. Funnily enough, Marianne also regularly leads these tours! You don’t need to sign up in advance, you can just look for the green t-shirts and umbrellas.

Of course, when I say “free”, I mean “tip-based”, so do remember to bring some cash with you. The free walking tours aren’t quite as much fun as the food tour because they don’t involve food and alcohol, but it’s still a fantastic way to explore Bo Kaap and learn about what makes this area so unique. 

Evening – Explore the V&A Waterfront

The V&A Waterfront is one of my favourite parts of Cape Town. There’s something about the energy here that’s decidedly upbeat, and it always makes me feel like I’m on holiday. 

(Living in Cape Town does feel like a permanent holiday, if I’m honest with you!)

There are some fantastic affordable restaurants here – my favourite being Life Grand Cafe – and I also love the sunset views from the Cape Wheel. If the evening isn’t too cold (or you’ve got a decent jacket), you can also watch the sun go down with a cocktail in hand at the famous Silo Rooftop

Day 2 – Wine Tasting + Time Out Market

Daytime – Go wine tasting 

Did you even go to Cape Town if you didn’t go wine tasting?

(Short answer: no!) 

I’m actually going to present you with a couple of different options for wine tasting today. I will say that my favourite is the Franschhoek wine tram, but honestly, all three have you in for a great day. And they all depart from and come back to the Waterfront! 

Option 1: Franschhoek wine tram 

The Franschhoek wine tram is probably the most famous (or should that be notorious?) way to go wine tasting in Cape Town. Although, of course, Franschhoek is about an hour outside of Cape Town, which is why I recommend booking this tour, which includes your wine tram tickets and return transport from the city. 

I did it with my friends and we had such an amazing day, and the tour worked out so much cheaper (and easier) than Ubering or trying to arrange overnight accommodation. What I like about the wine tram is that it’s hop-on, hop-off, so you can choose which wineries you go to and take the day at your own pace. 

I will say that the “wine tram” is a bit misleading because every route that I’ve done also involves a bus for at least half of the time. But still, it’s a lot of fun and you can do up to 5 wineries in a day this way, although we always stick to 4 so that we can enjoy a leisurely lunch. Quality, not quantity, am I right?

You can read my full guide to the wine tram here, or check out this article to see how it measures up to the Constantia wine bus. But this is the option I’d choose – I mean, it’s not every day that you get to go on a wine tram, is it? It cost R695 for the tour, but I ended up spending up R1,300 in total, because you pay for your food and wine on the day.  

Option 2: the Constantia wine bus 

The Constantia wine bus is also a ton of fun. It’s a hop-on, hop-off bus tour that takes you to the Constantia valley, where you can explore two or three different wine farms, and the Kirstenbosch botanical gardens, if you like. 

The route takes you to Groot Constantia, which is super cosy in the winter. I like the wine here the best, but for views, you just can’t beat Beau Constantia. I’ve done wine tasting here in the winter before, and the glass walls in the tasting room mean that cold weather doesn’t mean you have to miss those vistas! Fortunately, the wine bus stops directly outside of those two wine farms, and then you can work in either Silvermist or Constantia Glen – check out my guide to the wine bus for more on how to do that

The wine bus isn’t officially called “the wine bus”. It’s actually just the Blue Route of the hop-on, hop-off city sightseeing bus. I just book the generic ticket and then catch the bus to Constantia from the Aquarium. I’ve done this several times with friends who have come to visit in Cape Town, and they always love it! 

Option 3: Cape Winelands Explorer Tour

If you’re going for breadth rather than depth, this winelands tour takes you to Stellenbosch, Franschhoek, and Paarl. I think that this is a great way to explore these three legendary wine towns in a single day, and my friend, Liam, and I had such a great time on this tour. We went on a really hot day, though, and we both ended up getting really sleepy on the bus, so I think it could actually be even better during the winter!

The other two tours are hop-on, hop-off, so you and your group just kind of do what you please, whereas this tour is more structured. You’re in a big group and you all do the same tastings at the same time, which meant that Liam and I ended up meeting some wonderful people from all over the world. You can read my full length review here!

Plus, this tour was such a great way to learn about the Cape Winelands and their history. We also got a sabrage demonstration, a cellar tour, a cheeseboard, and a chocolate pairing, all included in the base price of the tour (R695, in case you were wondering). The only other thing we had to pay for was lunch. 

Evening – Dinner at the Time Out Market

All of the above tours will drop you back outside the Aquarium at the Waterfront, and what’s right nearby? Oh yeah, the Time Out Market!

The Time Out Market is the latest and greatest addition to Cape Town’s food scene and I must say, it does a fantastic job of collating many of the city’s (and surrounding towns’) best eateries under one roof. If you’re looking for something hearty to soak up the booze, I can’t recommend De Vrije Burger enough! People have been flocking to Stellenbosch for years to enjoy their famous burgers but now you can enjoy them right here at the Waterfront – and let me tell you, they’re totally worth the calories. 

Day 3 – Wildlife 

Morning – Boulders Beach 

You’ve probably heard about Cape Town’s famous penguins, and going to visit them at Boulders Beach is so much fun. I thought it might feel a bit gimmicky, but the beach is beautiful and it’s so well set up. You walk along boardwalks rather than on the sand so that you’re a safe distance from the penguins, which is good news both for them and for you, since they bite! 

To get to Boulders Beach, I recommend that you drive along Victoria Road through Camps Bay to Hout Bay, and then drive along Chapmans’ Peak. It’s an incredibly scenic journey and you’ll definitely want to pull over and snap some photos. There’s a R61 toll fee per car, and the road does close during bad weather so check the status before you go. If it’s closed, you can go via Constantia instead. 

Then, when you get to Boulders Beach, you will need to pay a R190 entry fee, which goes towards protecting these little guys’ habitat. I promise, it’s totally worth it. We even saw some whales breaching in the distance when we visited! 

For those without a rental car…

I love driving to Boulders Beach, but if you haven’t got a rental car, you can always book this half-day tour to Boulders Beach instead. Your driver will take you along Chapman’s Peak, so you get to experience that, and the guides are so knowledgeable about Cape Town. This option costs R1,280 per person, although you’ll still need to pay the entry fee on the day. It has almost 200 5-star reviews, so it must be good! 

Afternoon – Whale Watching Cruise 

The Western Cape is famous for its whales. In fact, seeing whales in Cape Town is one of the best reasons to come here in the winter. It’s really quite amazing – especially for someone who has lived most of their life inland, like I have. 

You can see humpback, Bryde’s, and Southern Right whales, especially between June and October. Now, the most famous place to go is Hermanus, which is said to be the whale watching capital of the world. However, that’s a 2-hour drive from Cape Town, so it’s not ideal if you’re only here for a few days. 

Fortunately, Simon’s Town is only 45 minutes south of the city – and Boulders Beach is actually in Simon’s Town, so you’re already here! Only one company operates tours here: the Simon’s Town Boat Company. They offer a whale and dolphin watching cruise during the winter, and you can snap up their 2 pm slot for R1450 per person. I think that this is such a great way to make the most of Cape Town at this time of year, and their sighting rate is an impressive 98%! 

Evening – Have dinner at Kloof Street House

I think that the final night of a holiday deserves a special dinner, so head to what I (and many others) consider to be Cape Town’s best restaurant: Kloof Street House! With a Gatsby-esque vibe and delicious food, this place is pretty much universally loved amongst Capetonians. If you’re a meat-eater, my advice would be to get the ostrich. Just remember to book a table.

They’ve got a great wine list at Kloof Street House, so you won’t go wrong there, and then if you fancy more drinks, no worries, because the restaurant is right in the heart of Cape Town’s nightlife scene. Kloof Street is home to so many fun bars. My favourite is Van Hunks, which has  a lively pub vibe, while Blondie is where the cool kids go and Ricks’ Americain is a good spot for rooftop cocktails. Asoka also does great martinis and really goes off on Tuesday nights in particular. 

Where to Stay in Cape Town in Winter

Tourists understandably flock to beautiful Camps Bay during the summer, but in the winter it’s quiet and doesn’t have that same fun vibe. Of course, that does mean you can snag better rates on luxury properties. For example, you can get a room at the top-rated and luxurious Atholl House for R4,900 per night rather than the R6,500 it would cost you during the summer – and with a 9.8 rating on Booking.com, you really can’t sniff at that! 

I always recommend staying in De Waterkant. It’s cheaper than Camps Bay and has a very quaint, European vibe with its pastel-coloured cottages and cobbled streets. It’s also one of the safest neighbourhoods in Cape Town, and it’s perfect for the winter because it’s home to so many cafes and cute bars where you can cosy up. I was lucky enough to live here for a while and I absolutely loved it. 

I’ve stayed at Home Suites Hotel in De Waterkant before and I can’t fault it. It was squeaky clean, very comfortable, and way more spacious than I had expected. You can snag rooms for as little as R1,480 per night during the winter, and even a little less with the Genius discount. I felt like I really got a lot for my money with this stay! 

Thanks so much for reading this blog! If you’re planning on visiting Cape Town during winter, I’ve listed a few more resources that you may find helpful…

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