Last Updated on June 12, 2026 by Hannah Stephenson
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!
Quick Overview
Day 1: Head up Table Mountain and then eat your way around Cape Town on a fun food tour!
Day 2: Go wine tasting in Franschhoek and then hit the Time Out Market.
Day 3: See the penguins at Boulders Beach and then go whale watching.
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!
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!
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 to try some South African classics. It’s 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 you 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, you can always switch the days of this itinerary around.
Read HUNDREDS of 5-star reviews and reserve your spot here!
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!)
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 have done this tour multiple times now, and it always works out to be so much cheaper (and easier) than Ubering or trying to arrange overnight accommodation. And it’s always an absolute blast, hence why I keep doing it!
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. You can read my full guide to the wine tram here!
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?
Check prices and book the Franschhoek wine tram tour here!
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!
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 – 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.
Where to Stay in Cape Town in Winter
Now that you have the perfect winter itinerary sorted, you just need a great place to stay! To make following this itinerary as easy as possible, I recommend staying in either Green Point or Gardens, as these are super central areas that are close to everything. I’ve got my top hotel picks in these areas below!
The Mount Nelson – $$$
The Mount Nelson is the grand dame of Cape Town. This iconic pink property is located just off of Kloof Street so it’s in an amazing location, and it delivers a very elegant stay. It’s super historic, and the service is truly world class. This is where all the celebs stay – seriously, even Queen Elizabeth II has been a guest here!
Rates start from R22,000 per night. Read the amazing reviews and book your stay here!
Kensington Place – $$
Kensington Place is a refined boutique hotel tucked beneath Table Mountain. Even though you’re in the city, you’ll be surrounded by greenery, whether you’re enjoying the view from your balcony or chilling by the pool. There’s also a cosy lobby area with a fireplace, which is lovely on cooler evenings, and the service is impeccable.
Rooms start at R5,000 per night. See all options and book your stay here!
Dysart Boutique Hotel – $
Dysart is a stunning solar-powered hotel in an unbeatable location. It’s in the heart of Green Point, putting you within walking distance of vibey Sea Point, the famous V&A Waterfront, and the pastel-coloured enclave of De Waterkant.
But a great location isn’t all that Dysart has going for it. It also boasts two pools, stylish decor, and a yummy breakfast spread each morning. You’ll never want to check out!
Rooms start from R2,400 per night. Find out more and snag your stay here!
You can check out more Cape Town hotel options here!