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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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Safari Bookings review

"A Truly Seamless African Adventure Adelle from Discover Africa was exceptional from beginning to end. She was knowledgeable, responsive and always prompt. She created an excellent itinerary with a perfect schedule, wonderful lodges and seamlessly coordin..."

Angela Kenedy, United States•15 Sep 2026•

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Trustpilot review

"My best friend and I just recently returned from an excursion in South Africa. There are simply not enough adjectives to describe this experience. Starting with the initial “interview” with Matthys Van Aswegen…. Matt was so thorough, so personable and extre..."

Teri May, Canada•31 Aug 2026•

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Google review

"My son Max and I just returned from an incredible trip to South Africa and Mauritus, and I can't say enough about how exceptional Susan Veldman was throughout the entire process. From the very beginning she listened to what we wanted and designed an itinera..."

Debby Anziano, United States•05 May 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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"Discover Africa and their trip advisor Megan Warrington did a fantastic job arranging our trip to Cape Town, Victoria Falls (Zimbabwe), and the Chobe River and Kwara Camp in Botswana. We originally planned this trip a few years ago, but had to cancel. Megan..."

Roger Pennifill, United States•12 Nov 2025•

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