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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

"We worked with Discover Africa to arrange our first ever Safari. Chrizaan from Discover Africa did a tremendous job in first understanding our requirements and wishes and then translating them into the perfect trip for us! Everything was organized to the..."

Elke Bregler, United States21 Apr 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 States17 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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Trustpilot review

"Megan Warrington was amazing to work with. She was very informative and kept us up to date on everything. I found out that I would need to have surgery a few days after returning from the trip and asked Megan if she would be able to arrange for a wheelchair..."

Carla Novak, United States09 Mar 2026

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"Adelle at Discover Africa helped to plan our first safari and everything went so smoothly from our internal flights to the game reserve and the booking at the lodge. Couldn’t fault them and wouldn’t hesitate to use them again in the future :)"

Amy MacDonald, United Kingdom01 Sep 2025

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"Susan took care of us from the planning to the experience itself. She was always available for us in answering questions and find best solutions. While on tour she kept in contact with us all the time. In terms of services, very well organized and reliable ..."

Carla, Italy26 Aug 2025

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