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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

"We travelled last August on a trip planned with Dev at Discover Africa. It was a family trip that i wanted us to remember forever and we definetly will! We could not have had an easier or more wonderful time and we would never have been able to plan and man..."

Megan Gray, United Kingdom16 Feb 2026

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"I had a great trip organised by Chrizaan. Everything went very smoothly including all of the pickups, flights and accommodation. I visited Namibia and loved seeing the dunes, springboks and oryx. I also visited the Okavango Delta and saw so many anim..."

Leanne Harrison, South Africa03 Feb 2026

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"Chrizaan Troch of Discover Africa helped us organize a recent safari in Chobe National Park. She was great to deal with - listened to what we wanted, and also offered other suggestions. She was very efficient, and always replied promptly to our questions. ..."

Celia Schroeder, Canada03 Dec 2025

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"We booked our safari through Chrizaan and the whole experience was absolutely fantastic. From the very beginning, communication was smooth and easy – both via email and WhatsApp – which made the planning process stress-free. Despite our limited availabil..."

Alejandro Martínez Hernández, Spain03 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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"We have returned again after Matthys arranged another trip for us for 2025, and we spent almost 4 weeks in May 2025, where we spent our time at Londolozi, Diulini Moya and Earth Lodge, and cannot thank Matthys enough. The camps we stayed at were once again ..."

Lana , Australia07 Aug 2025

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