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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?

Read recent reviews from travellers who have planned and booked their trips with us

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Trustpilot review

"Bianca, thank you for making this a wonderful trip. When we contacted Discover Africa we did not know what to expect. It was the best decision we could have made. The attention to detail made the trip go smoothly. When I asked a question, and there were man..."

Janet Orr, United States•29 Sep 2026•

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Google review

"My son Max and I just returned from an incredible trip to South Africa and Mauritus, and I can't say enough about how exceptional Susan Veldman was throughout the entire process. From the very beginning she listened to what we wanted and designed an itinera..."

Debby Anziano, United States•05 May 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 States•06 Apr 2026•

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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, Australia•10 Jan 2026•

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"Megan with Discover Africa did an excellent job planning our trip. We are from the US and it was so great to get her help. It made our trip so much easier. We flew into Cape Town and were there a few days. Then we were flown to Kruger National Park. Our sta..."

Catherine Hughes, United States•14 Oct 2025•

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"Susan and the team from Discover Africa you have excelled yourself through the initial contact to the very end of our journey. We were dazzled with the views of Cape Town. Victoria Falls and of course the game parks. The animals did not disappoint the spect..."

Andrew Wales, Australia•29 Sep 2025•

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