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Cape Winelands Vintage Sidecar Adventure

Africa's best authentic tailor-made safaris

Travel in a chauffeur-driven World War II vintage sidecar to the best wine estates in the heart of the Cape Winelands.

Do something different and visit Stellenbosch, Paarl and Franschhoek in the Cape Winelands in a chauffeur-driven sidecar. Enjoy wine tastings and a cellar tour without having to worry about drinking and driving. Feel like king of the road as superb mountain ranges, lush vineyards and Cape Dutch homesteads roll by.

From Cape Town you’ll take a leisurely drive towards the historical town of Stellenbosch. After a pleasant stroll through the town centre, it’s over the Helshoogte Mountain pass for a wine tasting at Tokara Wine Estate with its sweeping views across the valley.

After the tastings, load up your wine purchases in the sidecar and continue along the Helshoogte Pass to Boschendal Wine Estate for a cellar tour and wine tasting under the shady oak trees.

Then you’ll continue to Franschhoek, which dates back to the 17th century when the French Huguenots arrived. Billed as the Gourmet Capital of South Africa, this charming town in a pretty valley has French flair to complement the artistry of its chefs and winemakers. Take some time to enjoy the culinary skills of the chefs at one of the many award-winning restaurants (not included in the cost).

After lunch you’ll continue towards Paarl and Backsberg Wine Estate where you’ll have time to enjoy a wine tasting, meander through the cellar and relax in the beautiful garden. Then it’s back on the sidecar for a leisurely return to the city with Table Mountain bathed in afternoon sunlight.

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What Our Guests Have to Say?

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Trustpilot review

"The trip that was put together by Chrizaan Troch at Discover Africa was amazing. The accommodation was perfect as was the driving experience. This was our third self drive tour in Namibia and it was one of the best. Maps, accommodation, car, support all sea..."

Frank Morgan, Canada19 May 2026

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"I have been more than impressed with this entire experience every time. I will continue to use them year after year."

April Harrington, United States18 Dec 2025

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"We had a very well-organised itinerary by Chrizaan that suited our needs. It was a truly memorable holiday. Highly recommended."

Isaac, Malta22 Oct 2025

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"Cayleigh responded almost immediately to every question or concern that I had and resolved the issue quickly."

John M, United States08 Oct 2025

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"We just completed our second African safari planned by Megan Warrington, this one to Botswana, and we couldn't have been more pleased with our trip! Megan did a fantastic job of starting us out in the Kalahari (Tau Pan Camp) which was unique in its landscap..."

Darrh, United States09 Sep 2025

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"As soon as we chose Discover Africa to send us to Africa, we were constantly helped in planning the trip and were also continually guided during the trip. I felt as confident as possible that my wife and I were going to have a great trip. I appreciated the ..."

Greg Jacobs, United States16 Jul 2025

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