Few towns in South Africa weave history and modern living together quite as effortlessly as Stellenbosch, or Stellies, as it is affectionately known. Established in 1679 by Governor Simon van der Stel, it is the country’s second-oldest town and its beautiful centuries-old Cape Dutch architecture is not only preserved, but revered, with many buildings now home to contemporary restaurants, boutique galleries and local businesses. Yet despite its history, Stellenbosch never feels stuck in the past. Every visit uncovers something new, proving that the town is far more than just a wine destination.
Our latest visit reminded us exactly why a Stellenbosch getaway is always a good idea.
Get to Know Stellenbosch One Story at a Time
The perfect introduction to the town came with Stellenbosch on Foot, whose walking tours reveal a side of town that you simply wouldn’t discover on your own. Led by our incredibly knowledgeable guide, Johan Nepgen, we spent a fascinating morning wandering oak-lined streets while hearing stories that brought every building and corner to life.
It wasn’t just the dates and famous buildings that captivated us – it was the little stories that brought Stellenbosch to life. We learnt that the shapes above windows once formed part of a home’s address, allowing the postman to identify residents long before street numbering existed. We discovered that Stellenbosch was once effectively an island, surrounded by the Eerste River before sections were redirected over time. Then there was the famous cat statue, whose meaning and history we’d walked past countless times without ever knowing.
It wasn’t just the dates and famous buildings that captivated us – it was the little stories that brought Stellenbosch to life.
Seeing Stellenbosch through the eyes of someone so deeply passionate about its heritage transformed the town from just simply beautiful to fascinating. It’s an experience we’d recommend to every first-time visitor – and even locals who think they know the town well, you’ll be surprised by how much there is to learn.
Lunch At Terra
After our walking tour, Johan deposited us at the doorstep of Terra, located on Dorp Street, for lunch, where manager Miguel and his wonderful team made us feel immediately at home.
The menu is packed with dishes designed for sharing and every plate arriving at the table was better than the last. We loved the addictive prawn toast with kimchi, impossibly crunchy curried crispy chicken bites and a fresh tuna crudo with pineapple. This dish can optionally end with a shot of tequila, where you’re encouraged to drink the beautifully balanced pickling liquid straight from the bowl. Trust us – you will want to oblige!
But if there was one dish we’d return for tomorrow, it would be Ouma Mertia’s Pumpkin Tart, which can be a savoury side or a sweet finish. Rich, impossibly moist and delicious it was one of our favourite things we’ve eaten in a while. We’ll be going back for that when we next visit Stellies for sure.
A Stay at the Historic Lanzerac
If any property captures Stellenbosch’s ability to honour its past while embracing modern luxury, it’s Lanzerac.
As one of South Africa’s oldest wine estates, Lanzerac Hotel & Spa has centuries of history behind it, yet the estate feels relevant. The interiors, while formal, are elegantly decorated, balancing classic Cape charm with contemporary luxury.
Our room was exceptionally spacious and comfortable and filled with thoughtful touches like a complimentary mini bar with local wine and treats.
As one of South Africa’s oldest wine estates, Lanzerac Hotel & Spa has centuries of history behind it, yet the estate feels relevant.
The spa deserves its own mention too – an oasis of calm that perfectly complements the slower pace of Winelands life. It’s a balm to head down after a day of on-foot exploring and enjoy a warm spa bath.
One of the absolute highlights of our stay, however, wasn’t wine at all.
A Water Tasting That Changed How We Think about H20
At The Library at Lanzerac, we joined water sommelier Nico Pieterse for a guided water tasting – and it turned out to be one of the most unexpectedly fascinating hours of our entire trip.
Like most people, we’d always taken water for granted. But Nico demonstrated that not all water is created equal. From mineral content and mouthfeel to how different waters interact with wine, every bottle tells its own story.
We’re now those people standing in supermarkets reading the labels on bottled water in exactly the same way we read food packaging.
Perhaps most surprising was discovering how dramatically the right – or wrong – water can influence the taste of wine. It’s something we’d never considered before, yet once you experience it, you can’t unlearn it.
It was genuinely one of the most informative and enjoyable tastings we’ve ever done, and we’d wholeheartedly recommend adding it to any Stellenbosch itinerary.
A Winelands Lunch to Remember at Toevlug
The following day we headed to Toevlug, Bertus Basson’s beautiful restaurant at Annandale Wines.
Set on a family-friendly farm, Toevlug celebrates Basson’s Afrikaans heritage through thoughtful interiors and an approachable, proudly South African menu that feels both nostalgic and refined.
Chef Drikus Brink and the kitchen delivered a faultless lunch from start to finish. Highlights included beautifully prepared Blou Wildebeest tartare, outstanding yellowtail served with aji verde and Granny Smith apple that had us unapologetically wiping the plate clean with our fingers, before moving onto a perfectly cooked ribeye for sharing accompanied by ridiculously good triple-cooked potatoes.
We thought the savouries would be hard to top. Then came dessert. The pear and almond frangipane tart, served with crème anglaise and ice cream, was a dream – warm, buttery and utterly delicious
The Heart of the Winelands
The beauty of Stellenbosch is that no two visits are ever the same. You’re spoilt for choice with luxury hotels, boutique guesthouses, celebrated restaurants, casual cafés, award-winning wine estates and scenery that seems to stretch endlessly in every direction.
This trip reminded us exactly why Stellenbosch remains the heart of the Cape Winelands. It’s a place where history enriches every street, innovation keeps things exciting and exceptional food and wine are simply part of everyday life.
Even if we returned every weekend for the next year, we’d still only be scratching the surface of everything this remarkable town has to offer.
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