Stellenbosch: Wine tour with local guide & tastings

Summary

Small group wine tasting day with real Stellenbosch flavor

Spend your day exploring Stellenbosch’s vineyards with a local guide who knows every twist in the road. Taste wines paired with local cheeses, stroll through Cape Dutch gardens, and enjoy lunch overlooking the vines. With flexible stops and real conversations along the way, you’ll come home with memories (and flavors) that linger long after you leave South Africa.

What’s the experience like?

I thought I knew what to expect from a wine tour in Stellenbosch — but the first thing that hit me wasn’t the wine at all. It was the way the morning air smelled, kind of earthy and sweet, as we waited for our pickup outside the guesthouse. Our guide, Pieter, showed up right on time (he joked about “wine o’clock” being sacred here) and somehow made our little group of seven feel like old friends before we’d even left town.

The drive out to the first estate was quiet, except for Pieter pointing out which hills grew which grapes — I didn’t realize how much geography matters until he explained why some vines face east and others west. At Jordan Wine Estate, we wandered through gardens that looked straight out of a painting (the Cape Dutch gables are even better in person). The cheese and wine pairing was honestly a highlight; I still think about that salty blue cheese with their chenin blanc. I tried to pronounce “koeksister” when someone brought it up at lunch — Li laughed when I tried to say it in Afrikaans. Pretty sure I butchered it.

Lunch was casual, nothing fussy — just fresh bread and views over the vineyards at The Bakery. You could hear birds everywhere, and there was this soft breeze that kept blowing napkins off tables. After lunch, Pieter let us vote on where to go next; someone wanted more reds, so we ended up at a boutique spot where the winemaker himself poured our glasses. He told stories about Sutherland’s cold nights shaping their syrah — you could taste something wild in it, honestly. The whole day felt unhurried but full; not rushed from place to place like some tours I’ve done before.

By the last tasting my palate was confused but happy (is that a thing?). We all swapped numbers before heading back into Stellenbosch — funny how sharing a day like this makes strangers feel familiar so quickly. I keep thinking about those rolling hills and how different they look as the light changes — maybe that’s what makes Stellenbosch stick with you.

Step-by-step itinerary

Day 1 — Stellenbosch Wine Tasting Tour

• Wine tasting and garden walk
• Cheese and wine pairing tasting
• Lunch at The Bakery Jordan
• Tasting with winemaker at boutique estate

Top questions

How long does this Stellenbosch wine tour last?

The tour runs from 10am until 5pm.

Is pickup included for this wine tour?

Yes, pickup is included from your hotel or specified address in Stellenbosch.

How many wineries do we visit during the day trip?

You’ll visit three wineries for tastings during the tour.

Are food pairings part of this Stellenbosch wine tour?

Yes, food and wine pairings are included at one of the estates.

Is lunch included in the price?

No, lunch is on your own account at The Bakery or similar venue.

Can dietary requests be accommodated?

Yes, vegetarian options or allergy requests can be arranged if advised at booking.

What is the maximum group size for this tour?

The group size is limited to eight people.

Are children allowed on this wine tour?

The minimum drinking age is 18; no baby or infant seats are provided.

What’s included

Your day includes pickup from your hotel or chosen address in Stellenbosch, guided transport between three wineries with tastings at each stop (including one food and wine pairing), plus insights from a knowledgeable local guide before returning you to town by evening. Lunch is available for purchase during the midday break overlooking vineyard views.