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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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Trustpilot review

"Absolutely fantastic trip. Excellent accommodation. The Discover Africa team did a great job. Follow up and support while we were on safari. Vehicles was good. Drivers Excellent. Trip of a lifetime."

Anerie Du Toit, Portugal•14 Sep 2026•

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Safari Bookings review

"Adelle and team had plan my Africa trip according to what we discuss. They are professional and plan in detail the itinerary. We had a very good time in Africa travelling from Johannesburg, Victoria Falls, Botswana and end at Cape Town. The transfers are ar..."

Suhardi Semuni, Singapore•19 Jul 2026•

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"Booking with Justin at Discover Africa, to plan my safari and Victoria Falls adventure turned out to be the best choice I made. Right from the start, Justin was friendly, responsive, and incredibly thorough—he answered all my questions and provided a detail..."

James, Australia•24 Apr 2026•

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Trustpilot review

"All advising given by Discover Africa (in our case, by Justin Van Wyk) was really helpful and the programe they have outlined was great. Everything went really smooth and professional."

Luis Cortez, Portugal•15 Apr 2026•

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Trustpilot review

"Megan Warrington was amazing to work with. She was very informative and kept us up to date on everything. I found out that I would need to have surgery a few days after returning from the trip and asked Megan if she would be able to arrange for a wheelchair..."

Carla Novak, United States•09 Mar 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 Africa•03 Feb 2026•

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