Two full days in the City of Oaks – Stellenbosch

Posted on 27 March 2025

‘Stellenbosch has got wine and food, and activities to get your heart pumping and galleries to soothe your soul.’ writes Lorraine Kearney.

‘Known as Eikestad because of the many oak trees planted by its founder, Simon van der Stel, the historic town sits among hills and vineyards and is surrounded by significant magnificent mountains: Stellenbosch Mountain, Jonkershoek, Simonsberg and Botmaskop. Probably best known as the seat of Cabernet Sauvignon in South Africa, it’s also known for its Chenin Blanc. There are more than 200 wine farms in Stellenbosch, of which 126 are members of Stellenbosch Wine Routes.

ALSO READ: The South African small town that has it all

Start with breakfast and then walk

As with everything, Stellenbosch has coffee shops and cute places to grab breakfast in spades. Too many to mention here…

The best way to orient yourself and really get into the bones of a place is to walk its streets.

After breakfast, drop in at the Tourist Information Centre at 47 Church Street and pick up a map. We recommend a walk down Dorp Street and around the historic town centre.

Wine town

And it’s off to Cavalli Estate, with 26 ha under vine and 10 ha under indigenous flora. There’s a helipad here, too, and the estate works with Cape Town Helicopters to fly people in from Cape Town for wine tours.

 

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There are two tasting lounges, and a collection of memorabilia, such as guitars signed by The Rolling Stones and U2.

Settle in at the Tasting Terrace and sign up for the sorbet and wine pairing, or book a picnic on the grass for the First Friday sunset sessions when live music accompanies your sundowners – you can order a platter or dine at the restaurant under Executive Chef Lucas Carstens.

Blaauwklippen, the second-oldest wine farm in South Africa, offers wine pairings with pizza, chocolate, macaron and cheesecake.

There is also a pump track and the estate hosts various markets.

On the slopes of the Simonsberg Mountain, L’Avenir specialises in South Africa’s emblematic varietals: Pinotage and Chenin Blanc. Owned by the French leader of terroir wines, AdVini, its wines are sought-after locally and abroad.

Among these are a splendid Single Block Pinotage from a block of 35-year-old vines and a Single Block Chenin Blanc from a block of 51-year-old vines. We suggest the good old-fashioned cheese and wine pairing. Perfect.

Grab some grub

There are some of the finest dining options in the country-think Mill Street Bistro, Dusk Restaurant and Vuur... That said, there are plenty of casual eateries in town, too.

At Warwick Wine Estate, the Posh Picnic Pods are all about fine wine and fine-dining-style picnics in a serene, tucked-away setting. You can also go on a vineyard safari, with bubbles to ease the journey.

The Stellenbosch Reserve‘s restaurant is fringed by trees and looks out toward the mountains. The menu ranges from lamb ribs to aubergine melanzane and pizzas, and the salads are splendid.

Geuwels and Clara’s Barn, in the oldest barn in the Western Cape, are the two restaurants at Vergenoegd Löw. They fall under the ever-expanding umbrella of Chef Bertus Basson. Chef Drikus Brink is in the kitchen.

You can also watch the working flock of 1000 Indian runner ducks on their way to the vineyards, where they keep the farm pest-free, naturally. A walking trail, a herb garden and a children’s playground are also offered.

At Hartenberg Wine Estate, lunch is served in the courtyard garden and the tasting room. While you are eating, the children can happily – and safely -play in the picnic gardens. It’s all about regenerative farming here, and the estate has indigenous plants and wildlife, including more than 85 recorded bird species, duikers, steenbok and mongooses. There are also goats, sheep and Nguni cattle.

Get around

The Stellenbosch Vine Hopper is a hop-on, hop-off bus. There are three wine tour routes, each visiting five to six very different estates.

The Wine Tractor tootles around the Helderberg area. It also has three routes that take you along the back roads, through the vineyards, past the Nguni cattle and blue cranes. There are activities for kids.

 

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On your bike

Bikes n Wine offers several tours, such as the Vineyard Meander, a relaxed six-hour wine tour through three estates. Biking and hiking tours can be booked at VineBikes. The E-bike Winefarm Tour leaves from Lanzerac E-Bike Trail Centre and follows the Eerste River into town, then toward the Jonkershoek Valley to Stark-Condé Wines.

Put on your walking shoes

Stellenbosch Wine Walks has a leisurely 12 km wine walk starting at Ida’s Valley Nature Reserve, heading to Thelema for wine tasting and ending at Le Pommier for tasting and lunch.

The 8.5 km Blouklip Trail starts at Blaauwklippen and winds through winelands and natural habitats with expert guides. It takes you to Dornier’s modern art-inspired tasting area, for bagels and wines, and to Stellenzicht Wine Pod for a wine and chocolate pairing.

Nightlife

Two evenings a month, a section of Drostdy Street is closed for the Stellenbosch Street Soirées. Wine estates set up tasting stations and there is live music and food. But you need to book.

When the farms close for the evening, visit the town’s wine bars, among them Spek & Bone, under the oldest fruit-producing vine in Stellenbosch.

The Wine Glass – Stellenbosch offers more than 130 wines by the glass, by the bottle or simply in a tasting flight of six.

Art at heart

The Stellenbosch Art Mile is a public art space that stretches 1.6 km along the banks of the Eerste River. Wheelchair accessible, it crosses six bridges over the river, stretching from the pedestrian bridge on Krige Street at Markotter to the Coetzenburg bridge. The current exhibition’s theme is ‘Tapestry of Time’, and runs until September 2025.

Memorable moments

Rust en Vrede Wine Estate, established in 1694, is a historic gem in Stellenbosch, renowned for its exceptional red wines, particularly Cabernet Sauvignon and Syrah. Surrounded by the picturesque Helderberg and Stellenbosch mountains, the estate offers visitors a chance to experience memorable wines, world-class hospitality and the quintessential Winelands setting.

Guests can enjoy wine tastings and the winemaker’s lunch under the shady oaks, or experience fine dining at the acclaimed Rust en Vrede Restaurant, a top culinary destination. With a legacy of excellence, a visit to Rust en Vrede embodies a deep connection to heritage, terroir, and commitment to quality craftsmanship.

Award-winning charm

Stellenbosch Reserve, set in the heart of the Stellenbosch winelands, combines award-winning wines, Mediterranean-inspired cuisine, and stunning views for an unforgettable experience. Established in 2005 by Jean Engelbrecht, the winery produces the Stellenbosch Reserve wines that celebrate the region’s rich terroir. The new Tasting Room and Restaurant offer a serene blend of rustic charm and modern elegance, providing the perfect space to sample these distinctive wines. Signature dishes, such as wood-fired pizzas and slow-roasted Kalahari lamb, feature fresh, local ingredients. Stellenbosch Reserve invites visitors to savour the best of Stellenbosch’s food and wine heritage.

Take the children

Wonderdal at Hazendal combines advanced technological elements with creatively designed spaces to teach children topics from their school curriculum such as energy, nutrition and life skills. It’s interactive and aims to boost imagination, creativity and curiosity. There are trained supervisors on-site.

 

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Lay down your head

Bonne Esperance Guest House is a grand Victorian villa in a landscaped English garden. It’s just 500 m from the town centre with comfortable and well-appointed rooms. Nearby Middedorp Manor is a 100-year-old Victorian house with three en-suite bedrooms, outdoor entertainment spaces and a pool.

Article originally published in the December 2024 issue of Getaway Magazine. Find us on shelves for more! 

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