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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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"We contacted Discover Africa to help us plan my 40th birthday trip and we have no regrets. Justin organised the perfect trip and everything went so smoothly. Our trip was truly amazing and the accommodation options he suggested for us were all amazing in di..."

Gareth French, United Kingdom01 May 2026

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"Chrizaan arranged an amazing safari experience for six of us, who came from the UK and Australia. She secured our booking at a superb Lodge in the Kruger at relatively short notice, tied in the flight transfers and ensured that the whole experience ran smoo..."

Bethany Evans, United Kingdom10 Apr 2026

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"Matthys van Aswegen of Discover Africa went above and beyond to plan a two week trip for myself and my family (6 travelers) through multiple African countries that was unforgettable! There were many moving parts to our schedule, but every step was thorou..."

Ann Schall, United States08 Mar 2026

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"From start to finish, every phase of our trip was seamless. From the man who greeted us at Nairobi airport when we arrived to the woman who assisted us at our departure, we were taken care of perfectly. Our lodges at Saruni Samburu and Saruni Mara were beau..."

Lynne Calero, United States20 Nov 2025

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"Our safari trip to South Africa was nothing short of spectacular and I would like to thank Chrizaan for putting together a wonderful itinerary for us. Our first contact with Discover Africa was with a consultant who was amazing and very personable. Our plan..."

Rick, Canada15 Oct 2025

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"I had 2 months lead time to plan a Botswana safari so I googled tour companies. After emailing a few, I chose Discover Africa. Susan Veldman responded quickly and was able to figure out an 8 night safari, with stays in 3 different camps. Each one was amazin..."

Amanda, United States10 Sep 2025

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