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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

"I worked with Adelle on our travel itinerary and from start to finish she was incredibly. She arranged all flights, transfers, accommodations and tours perfectly! The accommodations and tours were beyond our expectations! The entire experience was seamless ..."

Elizabeth Conte, United States•28 Sep 2026•

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Google review

"Justin helped craft the perfect honeymoon for us! There are so many options when it comes to choosing a tour operator that I feel so fortunate we landed on Discover Africa. The experience felt seamless from start to finish. Our trip felt perfectly tailored ..."

Alex Dwornik, United States•17 Apr 2026•

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Trustpilot review

"For organising just a great trip. Every destination was different, but all the accommodation was first class. The managers were first class and always had my transfers in hand. Took the helicopter ride at Victoria Falls really add to the walk along the Fall..."

Eric Galloway, Australia•23 Mar 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 Kingdom•03 Feb 2026•

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"We had an amazing experience at Walkers Plains Camp. The wildlife viewing was superb from start to finish. Our guide Millie and tracker were super friendly, extremely knowledgeable and made the game drives an absolute pleasure. The camp was very luxuriou..."

Sue Panayiotes, United Kingdom•28 Dec 2025•

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"From start to finish, every phase of our trip was seamless. From the man who greeted us at Nairobi airport when we arrived to the woman who assisted us at our departure, we were taken care of perfectly. Our lodges at Saruni Samburu and Saruni Mara were beau..."

Lynne Calero, United States•20 Nov 2025•

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