The second oldest town in South Africa, Stellenbosch is known for its natural beauty and oak-lined avenues, Cape Dutch architecture, history and culture – and of course its wine routes.

Stellies – as it’s affectionately known – is a university town, so despite its heritage it retains a youthful vibe. They say you’re not a full-blown “matie” (Stellenbosch student) until you’ve been kissed in The Avenue, or until an acorn falls on your head. Both are relatively easy to achieve.

Surrounded by wine farms, the town is abuzz with hotels, wine shops, cafés, restaurants, boutiques, art galleries and museums. It’s quite small, so park your car and wander around on foot.

The Stellenbosch Wine Routes – the largest and oldest in the country – encompass more than 200 wine and grape producers in the region, which are divided into five sub-routes: Greater Simonsberg, Bottelary Hills, Stellenbosch Valley, Stellenbosch Berg and Helderberg, each with unique wines, climates and charm.

Spier offers a wide range of activities including Eagle Encounters, which has daily interactive shows with raptors; Segway tours of the vineyards and eco-friendly farm; picnics, tastings, markets and more.

Pop in at Delaire Graff Estate where the art, gardens and architecture will leave you breathless. The views from the top of the Helshoogte Pass are unsurpassed, the food is exquisite and the art collection impressive. It is here that the original Tretchikoff’s Chinese Girl resides, and Dylan Lewis’s towering cheetahs cast from solid bronze grace the estate’s landscape. Lewis’s distinctive work can be seen in the town’s streets as well, and at his own studio and sculpture garden in Stellenbosch.

At Middelvlei (Flamingo Road) you will meet the Momberg family and experience the way South Africans eat and socialise with a boerebraai (farm barbeque). The cosy tasting room has a welcoming fireplace in winter but you’ll have to compete with the farm dogs for the best spot in front of it.

Visitors in search of encounters off the beaten track can engage with the vibrant locals of Kayamandi Township through fun-filled tours on foot by Stellenbosch 360, the town’s tourism outfit, as part of its Route 360 cultural tourism initiative.

Rather than being a geographical route, Route 360, is a “people’s route” that paves the way into the hearts and homes of six Stellenbosch communities through authentic cultural experiences that offer visitors a colourful slice of the locals’ unique lifestyle, traditions and tastes. For more details visit the information centre at 36 Market Street.

Stellenbosch is home to many of the Western Cape’s top restaurants, most of which are on wine estates. Our recommendations for eating in town are De Warenmarkt food emporium, housed in an 18th-century building on the corner of Ryneveld and Plein streets. Part-artisanal-market, and part-restaurant, it features stalls including Ryan Boon (grass-fed speciality meats), Mano’s BakeryDeluxe CoffeeworksAround CheeseKan 10 street food, market bar Olive & Twist, and The Juice Revolution. Select your favourite bites and enjoy your meal at one of the communal tables.

In a similar vein is Schoon de Companje (corner of Bird and Church streets), which houses a butchery, a bakery, a fresh fruit and veg market, wine shop, a coffee bar, and a restaurant. Oom Samie se Winkel (Dorp Street) is an institution. This general store is crammed with a variety of vintage treasures and South African memorabilia.