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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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Trustpilot review

"From the very beginning, Bianca was a wonderful help in planning our South African safari. Her knowledge, attention to detail, and thoughtful recommendations made our trip truly exceptional. Becks Safari Lodge was, in our group’s opinion, a six-star expe..."

Leanne Morris, Australia12 Jun 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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"We had a truly magical safari experience perfectly planned & organised for us by Susan Veldman at Discover Africa. We flew from Cape Town to Hoedspruit and then seamlessly transferred to the most beautiful lodge in the Karongwe private game reserve. ..."

David Forbes, United Kingdom03 Feb 2026

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"Was just awesome, would recommend anytime...saw all big 5, all small 5, live kill by lions...was just divine"

Priyum Koonjul, Canada21 Nov 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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"We had a wonderful experience with Discover Africa and, specifically, Dev Panaino. Dev helped us plan a dream vacation to South Africa and Zimbabwe and made the planning from our end effortless. We met with Dev via Zoom calls for the initial trip planning, ..."

Sally, United States28 Aug 2025

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