Sex, Slaves and Song: An Unusual Walk Through Cape Town

Cape Town South Africa

I’ve been on about 4,312,131 walking tours in my life. Well, maybe not that many but definitely close to it. I like them on the whole, but lately I’ve been very picky about which ones I book. No longer am I content for a run of the mill experience and I will never ever take a free one again after the Debacle in Marseille. No, what I look for in a great walking tour is a unique angle, a fun way to learn about a city that I can’t necessarily find in guidebooks or on a tourism web site. I found what might be one of the most ‘out of the box’ tours on the planet when I joined the Sex & Slaves walking tour in Cape Town, South Africa as part of the #LoveCapeTown blogger trip.

The sun glimmered off of the buildings around Greenmarket Square in the center of Cape Town. Stands selling arts, crafts and trinkets were busy and the din of the city waking up echoed around the square. That’s where we met Dean, the flamboyant brains behind the Sex and Slaves tour. When I showed up I expected a standard walking tour focused on the early years of the city. What I got was a theatrical representation of those years.


Dean started the tours in order to provide a different way of learning about the city. Knowing full well that people remember the strange and unusual, Dean lapses into various characters, complete with costume and song throughout the experience. And experience is perhaps the best way to describe it. At first learning about the antecedents of modern Cape Town from a guy wearing a silly hat, hands clasped and singing is strange. No, it’s bizarre. But it works. I don’t know how or why it works, but it does. Walking around town that beautiful, sunshiny morning I finally saw nooks and crannies that I hadn’t seen before and learned more about the city than a book could ever impart.

That’s the beauty of a well-done walking tour. You get a local perspective; you see the city through their eyes. You learn what makes it great not from the facts and figures being thrown out like poorly aimed darts, but from the spirit with which they are thrown. There is no doubt looking at the glint in Dean’s eyes that he loves Cape Town, fiercely loves it. That pride was a recurring theme throughout my time in the Mother City, and perhaps that’s why I found myself loving it so very much. It’s hard not to love a city, to learn to respect it when everyone who lives there seem to be absolutely infatuated with their city.

So when you visit Cape Town, forget the boring, run of the mill tours and instead ask Dean to sing with you around town or even better, use this walking route I put together for you:

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

9 thoughts on “Sex, Slaves and Song: An Unusual Walk Through Cape Town”

  1. Thanks, Matt. This post has made me officially decide to quit my day job and give walking tours for a living. What a wonderfully perfect occupation.

  2. Drat! Just rang them to book the tour after reading this, and they’re no longer running it unfortunately.

  3. What a great article! Dean seems like a hoot. Thanks for including the pictures, especially the one with the mask. It’s a shame they’re not running the tour anymore (as per above) because I was definitely intrigued. I think your tip for trying to find a unique angle for a tour is a good one. I once had a friend who came up with a “Nitty Gritty Lima” tour which proved to be quite interesting.

    1. And I’m sorry for that, I’m investigating now what happened. If nothing else, it draws attention to 1)the beauty of Cape Town and 2)importance of finding off-the-wall tours.

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