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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

"My wife and I and two of our friends took this trip, which covered South Africa, Zimbabwe and Botswana. The trip was customized based on our needs and our Tour Manager/ Coordinator, Vihann, planned and executed with such ease and precision, I cannot think o..."

Ashesh, United States08 Jul 2026

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Safari Bookings review

"Discover Africa Safaris were great to deal with. Cayleigh put together an excellent itinerary which included Victoria Falls, Chobe National Park, the Okavango Delta and Maun. It included everything we requested, with excellent accommodation, transfers and s..."

Julie Whitmore, Australia09 Jun 2026

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"We had an amazing experience at Walkers Plains Camp. The wildlife viewing was superb from start to finish. Our guide Millie and tracker were super friendly, extremely knowledgeable and made the game drives an absolute pleasure. The camp was very luxuriou..."

Sue Panayiotes, United Kingdom28 Dec 2025

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"What we appreciated was the effort in doing all the best to satisfy our requests! So everything was as expected.. the tented camp (everything was like at home),the game drive( we asked a private tour), the position of the camp ( very important for us, we sa..."

Silvia Del Giovane, Italy12 Nov 2025

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"I chose a travel agency for four reasons. Years in business, quantity and quality of reviews, customisability, and local expertise. Discover Africa and my agent, Adelle, met or exceeded all expectations. I gave Adelle my budget and modified one of their sug..."

Thomas, Costa Rica12 Sep 2025

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"Susan took care of us from the planning to the experience itself. She was always available for us in answering questions and find best solutions. While on tour she kept in contact with us all the time. In terms of services, very well organized and reliable ..."

Carla, Italy26 Aug 2025

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