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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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"We have just returned from the most incredible 2 week trip in Africa, travelling to Kruger National Park, Cape Town and Victoria Falls - it was made all the more special by the incredible guidance, planning and organisation of Discover Africa, specifically ..."

Anita Panikkar, Australia10 Jan 2026

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"This was our first time going on a Safari, and also the first time using a travel expert to organise part of our trip. I was so impressed with how quick and easy the whole process was and Chrizaan tailored our experience to meet our travel needs whilst prov..."

Matthew Childs, United Kingdom18 Dec 2025

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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 have just returned from a trip to 3 different safari camps in Botswana, a short trip to Victoria Falls and a gorilla trek in Rwanda that was booked with Susan from Discover Africa. We couldn't be happier with the direction and support she gave us to trul..."

Robyn Dell, Canada02 Oct 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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"My daughter who is 27 and I (her mom)have been dreaming of this trip for a few years. It was everything we wanted July seemed to be the best month to visit South Africa. Weather is comfortable, better opportunity for seeing the wildlife , no mosquitos or bu..."

Laura W, Canada21 Aug 2025

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