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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?

Read recent reviews from travellers who have planned and booked their trips with us

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Trustpilot review

"Planning the trip with Bianca was a pleasure - she was patient and helpful and provided prompt answers to all our questions. The trip itself was remarkable, offering a wide variety of locations and experiences to make our exposure to Africa and safaris a..."

Barbara S., United States•18 Aug 2026•

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Trustpilot review

"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 Kingdom•01 May 2026•

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Trustpilot review

"We booked our safari trip through Justin van Wyk from Discover Africa, and we couldn’t be happier with the experience. He organized and booked everything from A to Z, so we didn’t have to worry about anything at all. Throughout the entire trip, we stayed..."

Gianluca, Switzerland•12 Apr 2026•

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"Megan with Discover Africa did an excellent job planning our trip. We are from the US and it was so great to get her help. It made our trip so much easier. We flew into Cape Town and were there a few days. Then we were flown to Kruger National Park. Our sta..."

Catherine Hughes, United States•14 Oct 2025•

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"This trip was all about making memories, and it did just that. Cape Town, Stellenbosch, Mala Mala Safari Lodge, Victoria Falls, and finally Zanzibar. Our boutique hotels along the way were nothing less than stunning, as was Lanzarac Manor in Stellenbosch. T..."

Angela Dandy, United Kingdom•24 Sep 2025•

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"We travel a lot. I don’t normally write reviews and I typically plan and book everything myself because I am very exacting when it comes to the itinerary, logistics, accommodations, activities, etc. – everything must be perfect. When planning this trip, I v..."

Debby Goosey, United States•18 Sep 2025•

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