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48 hours to Stay and Play in Stellenbosch this winter

Has winter got you feeling rather glum? We’ve got just the medicine to beat the winter blues – and all it takes is a 45-minute drive from Cape Town CBD to the warmhearted town of Stellenbosch.

Did you know there is an art to wintering?

While the dictionary may tell you that wintering is just a way to escape, spend or migrate the winter, we’ve made it into an art form. A lifestyle. An aesthetic. Winter is a season worth embracing, not escaping.

Enjoy a weekend getaway or linger longer and explore like a local. The Stellenbosch winter calendar of events is overflowing with new experiences, art exhibitions, restaurant and bar openings and heartwarming seasonal menus. We’re often blessed with many beautiful blue-sky days even in the depths of winter, but even on the gloomiest day, you can grab a brolly and enjoy the romantic ambience and European flavour of Stellenbosch.

  • – Cosy up next to a roaring fire, sipping on a glass of award-winning wine.
  • – Explore the historic oak tree-lined town centre, meandering through the quaint streets.
  • – Embark on a wine bar-hopping adventure, sampling the seasonal menus and winter specials.
  • – Engage in an art and cultural tour, discovering the rich heritage of Stellenbosch and surrounds.
  • – For the adventurous souls, venture out on mountain bike tracks, enjoying the crisp air and scenic beauty.

So go on, discover the art of wintering in Stellenbosch this season.

Here’s how you could spend 48 hours staying and playing in Stellenbosch this winter:

The streets of Stellenbosch boast incredible new public artworks, thanks to The Stellenbosch Outdoor Sculpture Trust (SOST)’s ninth annual public art exhibition running until March 2024. View all eight large-scale fine art photographs by acclaimed African photographers on your next visit. It’s a wonderful way to walk the town as well and get your bearings! Read more.
Top tip:
Pop in to
Petites Bulles Champagne Lounge (open from early!) for some brunch bubbles.


Who says picnics are only for summer? Experience the best of winter picnics at Spier, where a warm winter menu will warm you right up! The picnics can be enjoyed indoors or outdoors on the lawns on those delightfully blue-skied and sunny winter days.


Stellenbosch’s winter scene is flourishing with newly opened places, spaces, and offerings, adding to the town’s vibrant atmosphere. Explore the historic town centre and discover Le Chant Wine Bar and Petites Bulles Champagne Lounge, two exciting additions to the town’s growing selection of wine bars.

When night falls, kickstart your evening with sundowners at Nocturne, a trendy mixology bar sure to blow your mind with its innovative cocktails, or sample trendy Korean cuisine at Gochu Gang, a Korean food takeaway spot, both sister establishments to the acclaimed Dusk restaurant.

Browse winter restaurant specials here.

Immerse yourself in the culinary arts with renowned chefs and culinary masterminds during a series of captivating masterclasses. Get inspired by famous Stellenbosch local Bertus Basson as he discusses and demonstrates the creation of four delectable dishes as part of his masterclass offering. Indulge in the Stellenbosch Terroir Tasting, where you’ll unravel the fascinating influence of terroir on wines from the region. These masterclasses are just the beginning, with more delightful experiences to be announced soon!

Visit the Stay & Play website for more information.

With an overwhelming array of accommodation options in Stellenbosch and surrounds, visitors are truly spoilt for choice. Personally, we like cosying up next to a fireplace and indulging the “European” winter atmosphere of Stellenbosch at one of the many grand and historic manor houses or hotels, or a cosy B&B right in the heart of the walkable town centre.

Work off some of that good food and wine, hitting the many mountain bike trails. Choose whether you want to walk, hike, mountain bike or need a little assistance with an eBike.


If you’re more of a Culture Boscher, there’s lots more to enjoy in Stellenbosch, beyond just the wealth of galleries and fascinating museums.

Discover the culture and breathtaking surroundings of the Dwarsrivier Valley on a Pniël Cultural and Environmental Hiking Tour, guided by Pniël local Uhlan Lackay.
Or dine with a local in Kayamandi.

For a charming and relaxed final lunch in the Bosch, savour next-level pizza and casual fare at ‘biker bar’ Kantien, a new addition to Bertus Basson’s culinary empire, in the heart of town. Soaking up the winter sunshine dining on the porch is a wonderful experience.

BOOKMARK THIS! Wine Town Stellenbosch:
A highlight on the winter calendar, Wine Town Stellenbosch returns from 1-6 August 2023, offering an extraordinary wine experience. Delve into the world of wine with events such as the Cabernet Through the Ages Tasting at Waterford and the Le Riche Cabernet vertical vintages showcase. Indulge in delectable steak lunches at De Warenmarkt and join the Chenin Blanc takeover at the Wine Glass. The program is packed with unforgettable wine-themed events that will captivate wine enthusiasts.

Stellenbosch in winter will leave you enchanted. Whether you choose to chill at the OppiePlaas events on the picturesque wine farms or warm up at the lively InnieDorp offerings with art exhibitions, music performances, and culinary events, the only question to ask is: How are you going to spend your 48 hours wintering in the Bosch?Editor’s note: Visit Stellenbosch hosted a two-day media trip last month, inviting journalists and media from Cape Town to come and experience the art of wintering in Stellenbosch. View what the journalists got up to below: