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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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Google review

"Excellent trip -- tour operators were professional and on time. Safari lodge choices excellent. Adelle communicated issues that cropped up in a timely manner and the whole process was a pleasure."

Jake Sanderson, United States29 May 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, Portugal15 Apr 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 Africa03 Feb 2026

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"I was recommended Discover Africa by a friend who raved about them for their African Safari adventure and they didn't disappoint. From the start the communication was timely, despite the time zone difference, and the advice was thorough and precise. It seem..."

Stephen Suster, Australia18 Jan 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 did a 3-week bespoke tour with Discover Africa and specifically Devryn Panaino. South Africa, Zimbabwe, Botswana game parks. Our group of 6 had a fantastic time, as the itinerary was top notch, transfers smooth and now we can’t wait to go back. We were n..."

Vicki, Australia08 Sep 2025

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