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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

"Chrizaan was wonderful. She took our requests to heart and created a once in a lifetime trip for us. The transportation was arranged flawlessly and the safaris were breathtaking. We saw so much and did so much but it didn’t feel rushed. I would recommend Ch..."

Jacqueline Berkebile, United States28 May 2026

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Trustpilot review

"The trip that was put together by Chrizaan Troch at Discover Africa was amazing. The accommodation was perfect as was the driving experience. This was our third self drive tour in Namibia and it was one of the best. Maps, accommodation, car, support all sea..."

Frank Morgan, Canada19 May 2026

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Trustpilot review

"We had an amazing safari experience in Botswana thanks to Chrizaan! She planned everything perfectly and was very professional, honest, and helpful throughout the entire trip. She supported us every step of the way and was always available whenever we ne..."

Mojgan Owliaey, Germany18 May 2026

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Trustpilot review

"Working with Susan made our experience just perfect. She has everything organized and it all went so well. Her recommendations were perfect. We loved the safaris she chose, the lodges, guides, staff and the experience were wonderful."

Marlene Wheatley, Canada22 Mar 2026

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"Cayleigh planned the perfect safari for us! The safari and tour following were exactly what we wanted. Rockfig was an amazing luxury experience that allowed us to see the big 5 and so much more. Our trip with Discover Africa was worth every penny!"

Alan Kane, United States01 Dec 2025

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"We just completed our second African safari planned by Megan Warrington, this one to Botswana, and we couldn't have been more pleased with our trip! Megan did a fantastic job of starting us out in the Kalahari (Tau Pan Camp) which was unique in its landscap..."

Darrh, United States09 Sep 2025

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