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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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Google review

"Excellent trip -- tour operators were professional and on time. Safari lodge choices excellent. Adelle communicated issues that cropped up in a timely manner and the whole process was a pleasure."

Jake Sanderson, United States•29 May 2026•

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Trustpilot review

"The trip that was put together by Chrizaan Troch at Discover Africa was amazing. The accommodation was perfect as was the driving experience. This was our third self drive tour in Namibia and it was one of the best. Maps, accommodation, car, support all sea..."

Frank Morgan, Canada•19 May 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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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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"Justin Van Wyk from Discover Africa Safari did an outstanding job in planning our perfect Safari. All travel and transfers between airports and game lodges have been flawless! The lodges and safari experiences have been awesome."

Roland Braun, United States•05 Jan 2026•

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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 States•12 Nov 2025•

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