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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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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

"Chrizaan arranged an amazing safari experience for six of us, who came from the UK and Australia. She secured our booking at a superb Lodge in the Kruger at relatively short notice, tied in the flight transfers and ensured that the whole experience ran smoo..."

Bethany Evans, United Kingdom10 Apr 2026

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Google review

"This was the most thrilling vacation I have ever taken. Justin at Discover Africa planned everything down to the finest detail so it was effortless, magical and perfect from start to finish. A trip of a lifetime and then some!"

Heili Lehr, United States06 Apr 2026

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"I have been more than impressed with this entire experience every time. I will continue to use them year after year."

April Harrington, United States18 Dec 2025

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"Vihann was responsive and friendly, worked patiently with me as I tweaked my itinerary three times. I researched the camps myself and Vihann supported with his local knowledge so the result was very memorable and extraordinary holiday. I was very happy with..."

Aarti Sharma, Australia10 Dec 2025

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"I chose a travel agency for four reasons. Years in business, quantity and quality of reviews, customisability, and local expertise. Discover Africa and my agent, Adelle, met or exceeded all expectations. I gave Adelle my budget and modified one of their sug..."

Thomas, Costa Rica12 Sep 2025

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