Stellenbosch: Private Wine Tour & Cheese Tasting with Pickup

Summary

Stellenbosch wine tasting with cheese pairing and cellar tour

You’ll taste wines straight from Stellenbosch cellars with someone who knows their way around both vineyards and stories. Expect cheese pairings, relaxed lunch stops (with time to explore), and even chocolate matched with reds—all with private pickup so you can just focus on what’s in your glass. It’s more about feeling welcome than knowing all the right words.

What’s the experience like?

“If you swirl it just right, you’ll catch the fynbos in the nose,” said Pieter as he handed me my first glass in Stellenbosch. I tried to copy his wrist motion but mostly ended up splashing a bit on my thumb—he grinned and shrugged, like this was all part of the fun. The air outside smelled faintly of eucalyptus and sun-warmed earth, and even though I’d read about South African wines before, actually standing in that old cellar felt different. There was a quiet hum from the bottling room next door, and I remember thinking how much work goes into every bottle we taste in a hurry.

Our guide (who seemed to know everyone at each estate) kept things light—no snobbery, just stories about the families behind the labels and how the soil changes everything. At one stop we paired sharp local cheese with a Chenin Blanc that tasted way brighter than anything I’d had back home. Someone at our table tried to pronounce “Koeksister” and got a round of laughter from the staff—there’s an easy warmth here that makes you forget any nerves about not knowing your tannins from your terroir. The private wine tour through Stellenbosch didn’t feel rushed; we lingered under big oak trees between tastings, and honestly, I could’ve sat there for hours just watching the clouds move over the mountains.

Lunch was casual—nothing fancy, just good food (I went for something with biltong on top because when in South Africa…) and plenty of time to chat or wander around. By the time we reached the chocolate and wine pairing, my palate was probably shot but I didn’t care; there’s something kind of perfect about ending a day trip like this with sticky fingers and laughter echoing off old stone walls. The drive back was quiet except for Pieter humming along to an old Johnny Clegg song on the radio. I still think about that view from the last vineyard—late afternoon light catching on rows of vines—and how it felt both familiar and totally new at once.

Step-by-step itinerary

Day 1 — Full day Stellenbosch wine tasting tour

• Wine tasting
• Cheese and wine tasting
• Lunch stop (own account)
• Chocolate and wine tasting

Top questions

Is hotel pickup included in this Stellenbosch wine tour?

Yes, private transportation with pickup and drop-off is included.

How many tastings are included on this day trip?

The tour includes several wine tastings, plus cheese and chocolate pairings at different stops.

Do I need to be a wine expert to enjoy this private tour?

No prior wine knowledge is needed—the guides make it accessible for everyone.

Is lunch provided during the Stellenbosch wine tour?

The lunch stop is included but food is at your own expense; options depend on availability.

Are children allowed on this private Stellenbosch wine tour?

Yes, infants and small children can ride in a pram or stroller.

What’s included

Your day includes private transportation with pickup and drop-off, all tasting fees at each winery—including guided cellar tours—plus cheese and chocolate pairings along the route; lunch is not included but there’s a stop arranged so you can order what you like before heading back through those vineyard roads home.