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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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"Justin helped us with the safari and Victoria Falls portion of our trip to South Africa, Botswana and Zimbabwe. The lodges were fantastic and ground transfers perfectly executed. We had an amazing time!"

Kelly Headrick, United States02 Jun 2026

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"We had a great trip in Namibia. In 11 days we did a roundtrip, which was organised through online meetings. Every thing went on as agreed on and ver smoothly. We had a very good guide/driver, who explained us a lot about the country, politics, history and m..."

Peter Esslinger, Switzerland30 Nov 2025

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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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"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 States14 Oct 2025

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"I started planning my Africa safari/vacation about two years ago with the help of Diane, and was transitioned to Chrizaan about halfway through my timeline. There was zero issues with changing my guide, and both ladies were SUPER lovely to work with. I was ..."

Kaleigh Gray, United States02 Oct 2025

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"We booked our safari adventures in Kenya and Tanzania with Susan at Discover Africa. The trip was nothing short of amazing, one of the best safari experiences we have ever enjoyed. Susan was thoughtful and patient throughout the planning process and really ..."

Cathy Hurdle, Thailand28 Sep 2025

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