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Looking for the perfect Cape Town itinerary? Cape Town has plenty of things to do and one of the most dramatic cityscapes in the world, one that merges seamlessly with mountain and sea. Located close to the southernmost tip of Africa, the city stretches along a thin peninsula culminating in Cape Point, a treacherous rocky formation whose unpredictable currents have shipwrecked countless vessels on their way to the Indies. In order, to see the main highlights, and enjoy some Cape Town excursions, I usually recommend a minimum of 5 days in Cape Town.

Doubling the Cape was a feat for 17th centuries seamen, who were then given time to celebrate on dry land and resupply with fresh produce from Company’s Gardens, in what today is Cape Town’s city center. Here they also built churches, a castle, and houses in the typical ornate colonial style that became known as Cape Dutch.

During the following centuries, waves of immigrants, both voluntary and non, came to swell the old town, which then expanded out from the area nestled between Table mountain, Lion’s Head, and Signal Hill towards the Cape in the south, the Atlantic coast in the north, and as far as the eastern marshes near the Hottentot mountains.

Cape Town is thus an amalgam of dramatic natural beauty and rich cultural history, all of which I will show you in this five days in Cape Town itinerary. I promise that you will fall in love with Cape Town, like I did while living there on and off these last few years. For those curious, I spend my time living between South Africa, Cuba and Europe.


What to pack for Cape Town

It depends on the season. The best time to visit is November to April, when you will be guaranteed sunny days and a gentle breeze. Unless you like dramatic weather, in which case pick the months between June and September to enjoy thundering clouds punctured by the occasional blue sky.

It never gets seriously cold though, so pack long sleeves, an umbrella, and fall jackets but leave your moonboots (snow boots) at home. Whatever the season, don’t forget a couple of smart outfits for wining & dining, as well as sporty gear to explore the Cape’s natural wonders.

Getting there

Cape Town really is at the far end of the world, with only a few direct flights to Europe and none to the United States. But Johannesburg, which is only two hours away, is a major transport hub, with hundreds of daily connections to all five continents.

TIP: I usually use Skyscanner to check the best flight options. They have tons of deals.


Getting around Cape Town

Public transport is not the Mother City’s strongest suit, so to move around town I recommend using Uber, which is safe, cheap, and readily available.

On the other hand, renting a car is a must on outdoors-focused days, unless you decide to go for an organized excursion. I usually book most on GetYourGuide. Check out some options below!

Where to stay in Cape Town

Airbnb is currently Cape Town’s largest hospitality provider due to the high quality of the city’s housing stock and its competitive prices.

The best areas to stay in are the CBD, the hilly neighbouring suburbs of Vredehoek, Tamboerskloof, Oranjezicht, and Gardens, and the Atlantic Seaboard (Green Point and Sea Point), which are also where most of Cape Town’s best hotels are located. For a California-like beach feel you can stray as far as posh Camps Bay.

The perfect 5 days in Capetown Itinerary for first-time visitors

Cape Town Itinerary - 5 days in Cape Town excursions + activities

DAY 1 – Get to know the city (Table Mountain, Bo Kaap, Long Street)

Rise with the birds on your first day in town to climb Table Mountain, one of the world’s new seven natural wonders. The best time to start tackling the two and a half-hour ascent is between 6 and 7am, when you won’t be eerily alone but neither will you have to queue at every rope.

If it sounds hard, well, it is not a literal walk in the park, but so worth it! The vista from the top is astounding. Those who can’t or won’t leg it to the summit can take the cablecar on their way up as well as down.

Price is R290 return and queues long, so either way, make Table Mountain an early morning endeavor. And don’t forget to take a picture on its iconic lookout rock. The drop is actually a padded, gentle slope, so not as hair raising as it appears!

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Once you are safely back at sea level you can regroup in one of the city bowl’s seemingly infinite cafes. Cape Town is big on healthy breakfasts, so whichever your choice, you won’t be disappointed.

From Tamboerskloof or Bree Street, the heart of morning eats, walk up to Bo Kaap, a traditional Cape Malay neighborhood consisting of brightly painted little houses.

Here is where Malaysian workers from South East Asia came to live in the 18th century. Perhaps because of the community’s cohesion or maybe just out of sheer luck, they managed to escape the forced relocations of the high apartheid era and today still comprise the vast majority of the area’s inhabitants.

If the climb has made you hungry, this is also your best opportunity to taste an authentic Cape Malay curry at Biesmiellah.


After a wash and a rest at your lodgings, head to Long street for a night of partying in Cape Town’s entertainment street. The strip isn’t one of the city’s most sophisticated spots, but it has plenty of options for both eating and drinking – especially the latter.

If you want to have dinner in the area too, I recommend tapas at Fork, Italian at Carne, and sushi from Minato. You can then choose from hundreds of brews at Beerhouse or dip into local wine culture at Orphanage or V Bar.


DAY 2 – Winelands (Stellenbosch & Franschhoek or Constantia)

After a hectic first day you may wish to take it easy. And what is a better way to relax than sampling great wine in the bucolic Cape countryside? Depending on whether there is a near teetotal driver amongst your travel companions, you can book a tour or rent a car.

Private tours start from around R1000 per person but can drop to R500 for groups. You will be taken to 3-4 wine estates in the Stellenbosch-Franschhoek region and supplied with enough wine to ensure you’ll be singing in all of South Africa’s eleven official languages by the time you start back to the city.


If you wish to stay closer to Cape Town, you also can jump on the local hop-on hop-off sightseeing bus and take its aptly named purple line to explore Constantia’s wine estates.

There is no difference in the quality of the wineries, so this is a good option for those with a smaller budget and without a self-sacrificing driver. One-day tickets cost R200 and wine vouchers, for which you will get between 3 and 7 tasting glasses depending on the category you choose, around R50.

I recommend that you try South Africa’s signature grape, Pinotage, and go for a stroll through the vineyards before your horizon line gets blurred. The wine is that good!

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DAY 3 – Peninsula Tour (Kalk Bay, Simon’s Town, Cape Point, Hout Bay, Camp’s Bay)

This is another excursion for which you can choose between a guided tour and renting a car.

Since there is a low risk of drink-driving involved here, I strongly recommend the second option. Rentals are cheap, and the Western Cape is really one of those regions that lands itself to be explored without a strict timetable.

Having said that, since the itinerary is quite long (about 150km), you should have an indicative plan and make an early-sh start.

Assuming that you are leaving from the city bowl or the Atlantic seaboard, which by the way are the areas in which you want to find lodgings, it will take you about an hour to get to Kalk Bay, where you can have a late breakfast at Olympia cafe or an early oyster lunch at Harbour House.

If you would rather push on, grab some delicious fish & chips at Kalky’s and then drive to Simon’s Town.


Boulders beach is possibly the only place in the world where you can swim with penguins in the wild. Because if water temperatures aren’t exactly the Caribbean (they hover between 12 and 16 celsius degrees), at least you won’t have to dodge icebergs.

After taking the obligatory pictures, you can start back on your journey to Cape Point… before checking the bottom of your car for stray penguins, of course.

Boulders Beach

As soon as you enter the national park, start scanning the horizon for ostriches and baboons. In fact, be very careful around the latter, as they move in gangs and engage in an occasional violent crime such as purse snatching.

True story. You then need between one and two hours to walk up to the lighthouse, drive down to the Cape of Good Hope, and out of the park.

On your way back, coast the other side of the peninsula via Hout Bay (have a snack at the fish market or find a guide to show you around Imizamo Yethu, the local township), the scenic Chapman’s Peak, and Camps Bay.

Here you can conclude this nature-soaked day with a very urban dinner at Zenzero. But don’t worry, “urban” in Cape Town still includes activities like watching the sky turn pink as the sun dips into the ocean.

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Hout Bay, Cape Town in South Africa

DAY 4 – Apartheid South Africa (District’s 6 Museum, Robben Island, Waterfront)

After a couple of outdoorsy and pretty hedonistic days, it’s time to learn more about South Africa’s fascinating albeit sad history. Energized from breakfast at Truth, the king of steampunk coffee in South Africa, cross Buitenkant Street for District 6 museum.

Looking at the anonymous commercial buildings behind it you would never guess that until the 1970s the area was a vibrant and densely populated residential neighborhood, one of the most diverse in the country.

The museum offers a glimpse into family and community life during that era, before the apartheid regime forcefully relocated the district’s inhabitants to the distant and inhospitable Cape Flats.

Your next stop on your educational day out is Robben Island, South Africa’s version of Alcatraz and Nelson Mandela’s home for 18 of the 27 years he spent behind bars as a political prisoner. A former political prisoner like him will be your guide, something that adds an extra emotional layer to an already intense experience.

On the island, you will be shown Mandela’s cell and his measly diet, as well as the limestone cave where he was forced to work until his eyesight almost gave up. Tours to Robben Islands depart four times a day from the V&A Waterfront. Price is R360 and advance booking essential.


Back at the Waterfront and more culturally aware than when you left the house in the morning, you can now fall back into unbridled debauchery by shopping for high-quality souvenirs and dining at one of the mall’s excellent restaurants.

TIP: I recommend you to taste the best sushi in town at Willoughby’s and shop for beautifully crafted textiles and woodwork at the Watershed.

DAY 5 – Unusual pursuits

For your last day in Cape Town, I planned two fringe activities: a visit to the heart transplant museum and paragliding.

Start your morning with a hearty English breakfast at Bacon on Bree, then take yourself to the grounds of Groote Schuur hospital to learn what you just did to your heart.

Part Madam Tussaud’s and part house of horrors, the museum offers an insight into the life and work of Christiaan Barnard, whose groundbreaking heart transplant in 1967 divided the world into two camps: one side there were those in awe at the miracle, on the other people dismayed at what they saw as an attempt to give Frankenstein a brother.

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Christiaan Barnard - cardiac surgeon - first heart transplant

At the museum, you will learn about the politics of race in apartheid South Africa and those of science at large. You will look at diseased hearts in formaldehyde and read a fine selection of the threatening letters received by Barnard and his team.

Most weirdly, you will get a chance to hold the hand of Mr. Washkansky – wax version – while he recovers in his hospital bed.

hold the hand of Mr Washkansky – wax version in Cape Town Africa

For your last Cape Town afternoon head back to the city bowl and up to Signal Hill.

Here is where for around R1200 you can jump off a steep sea-facing slope and bid farewell to this spectacular city in the most spectacular way.

Or if the visit to the transplant museum made you think twice about mistreating your heart, just uncork a bottle of Pinotage and watch the antipodean sun set on the sea from the safety of your picnic blanket.

This is a guest post by: Barbara from the travel blog

AUTHOR’S BIO: Barbara went to university to study geography because she wanted to see the world. Twenty years and twenty times as many adventures later she is living her dream. When she isn’t evaluating development programs in exotic locations, she runs a travel blog and spends her time between Europe, South Africa, and Cuba.

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