The Points Guy Brian Kelly
Photograph: The Points Guy
Photograph: The Points Guy

The Points Guy: Why I love Cape Town

Travel expert Brian Kelly, founder of The Points Guy, shares why Cape Town is his favourite city in the world...

Richard Holmes
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Brian Kelly knows a good deal when he sees one.

As founder of the global travel media platform The Points Guy, Kelly has revolutionised the way consumers use loyalty points and credit card spending to fund their travels. What began in 2010 as a personal blog—a side hustle from his career in finance—has rapidly evolved into a global juggernaut. Today, more than 11 million travellers turn to his website each month for help in how to travel smarter.

His first book, ‘How to Win at Travel’, was released in February 2025 and soared straight onto the New York Times’ bestseller list, leading the way for travellers to leverage airline and credit card points for planning their dream holiday. And where does the man himself like to go on holiday?

It turns out that Kelly's dream holiday is to book a flight straight to the Mother City! In a recent interview with the New York Times, he named Cape Town his favourite city in the world. So, of course, Time Out Cape Town had to track him down and find out why! 

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This article was written by Richard Holmes, a travel writer based in Cape Town. At Time Out, all of our travel guides are written by local writers who know their cities inside out. For more about how we curate, see our editorial guidelines and check out our latest travel guides written by local experts.

The Points Guy's guide to Cape Town

What first brought you to Cape Town?

My first trip was in 2013, when I came to South Africa for my first safari. It was my first time in Cape Town, and I immediately fell in love!

What were your first impressions?

The physical beauty stood out to me from the beginning. On my first trip, I went to see Table Mountain (and the magnificent tablecloth of Table Mountain), go great white shark diving in Gansbaai, and just explore the area as much as I could. Cape Town has this incredible majestic quality that never ceases to amaze me.

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The one thing that surprised you?

The food scene… It’s always evolving and there are so many great restaurants to try with every visit. I love The Pot Luck Club. It’s a super unique venue with delicious food, great drinks and an overall great vibe. The Delaire Graff Estate is another favourite with gorgeous views, superb wines and fresh, artisanal food that pair perfectly together.

Which is your favourite hotel in the city?

The Silo Hotel is my favourite place to stay. It has everything you want in a hotel: magnificent views, close proximity to the waterfront, really cool rooms and great service.

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Your favourite day out?

There are so many to choose from! I’ve paraglided off Signal Hill, gone on countless hikes and had so many magical experiences in Cape Town. The last time I was there, I came across a puffadder on a trail by Lion’s Head. That was definitely a wow experience, and thankfully, the locals made sure I knew to stay far away!

One moment you won’t forget…

Bringing my son to Cape Town and seeing a place I already loved through his eyes. I’ll never forget the time I took him to Boulders Beach and a dassie stole one of his socks. The dassie is his favourite animal to this day! We have a stuffed dassie from the Table Mountain Shop and that’s always a fun story to tell his American friends, who often don’t know what dassies are.

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Favourite day-trips beyond the city?

Wine country is just absolutely spectacular and is still one of my favorite things to do since my very first trip. During my last visit, I stayed at La Residence, which is an out-of-this-world property with just incredible, magical views.

The best places for travellers to spend points?

Cape Town has a bunch of great points hotels to choose from, including Hyatt, Westin, Hilton and more. The Hyatt Regency in downtown Cape Town is especially great for budget travelers with some rooms available as low as 6500 points per night.

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Bang for buck?

In terms of value for money, Cape Town is a great and affordable destination for Americans because of the strength of the US dollar. The hotels in Cape Town offer a ton of value for travellers, whether they’re booking with points or cash. Not only does the Hyatt Regency in Cape Town offer rooms for 6500 points per night, but one of the writers for The Points Guy stayed at that same hotel for $80 per night a few years ago!

Your favourite airline into Cape Town?

Convenience is key, so flying direct from Newark to Cape Town on United is hard to beat. But if I’m not in a rush, I love taking Emirates through Dubai on my way to Cape Town.

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What’s Cape Town like for kids?

As a parent who’s visited with a toddler, I can personally vouch for Cape Town being an incredible kid-friendly destination! My son Dean still talks about the time a dassie stole his sock at Boulders Beach and we had a great time just walking around, seeing penguins and taking in the views. Plus, there’s hiking, a fantastic aquarium and so much more that I can’t wait to experience with Dean again the next time we go to Cape Town.

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