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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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"We had an amazing time, and loved every minute. The tour was very well planned, and dealt with the many changes we made with ease."

Eric van Lent, United States22 Feb 2026

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"Chrizaan Troch of Discover Africa helped us organize a recent safari in Chobe National Park. She was great to deal with - listened to what we wanted, and also offered other suggestions. She was very efficient, and always replied promptly to our questions. ..."

Celia Schroeder, Canada03 Dec 2025

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"Very professional; quick to respond. The trip itself was fantastic. The lodging and the game drives were great. Guide was great; he anticipated where hard-to-find animals would show up. Lodge staff were very friendly. Food was great. "

Akos Ledeczi, United States12 Nov 2025

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"Discover Africa planned a fabulous trip for us! The travel planner came up with an itinerary that included everything we wanted; the trip was extremely well organized; the accommodations were lovely; and the activities were fun and interesting. We especiall..."

Kim Bixenstine, United States30 Sep 2025

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"We booked a safari through Discover Africa for Botswana and Zambia and it was fantastic! Chrizaan was super helpful and accommodating, especially when we had to change our dates of travel slightly. She worked with the lodges to accommodate us and found a so..."

Alice & Ross, Monaco09 Sep 2025

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"A Truly Unforgettable Journey – Thank You, Megan! I wanted to give a special thanks to Megan for planning such a wonderful trip for us. Our adventure began at the breathtaking Victoria Falls and continued to the stunning Chobe Lodge — what an amazing experi..."

Lorena, Italy07 Aug 2025

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