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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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Safari Bookings review

"Adelle and team had plan my Africa trip according to what we discuss. They are professional and plan in detail the itinerary. We had a very good time in Africa travelling from Johannesburg, Victoria Falls, Botswana and end at Cape Town. The transfers are ar..."

Suhardi Semuni, Singapore•19 Jul 2026•

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Trustpilot review

"As a party of seven guests we found the travel arrangements seamless and the accommodation well suited to both older and younger members. In addition, we were of mixed bush experience with some seasoned safari members and some first timers. The Lodges and e..."

Jenny Ashley - Smith, Canada•18 Mar 2026•

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Safari Bookings review

"A trip of a lifetime. Great guides covering Tarangire National Park, Lake Manyana, Ngorongoro crater and southern Serengeti, where we saw herds of elephants, giraffes, antelope, zebra, wildebeast, cape buffalo, eland, jackels, hyenas, mongeese, hippopotomi,..."

Paul Couch, United Kingdom•16 Mar 2026•

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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 States•22 Feb 2026•

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"Cayleigh planned the perfect safari for us! The safari and tour following were exactly what we wanted. Rockfig was an amazing luxury experience that allowed us to see the big 5 and so much more. Our trip with Discover Africa was worth every penny!"

Alan Kane, United States•01 Dec 2025•

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"We truly cherished every moment of our trip—there are countless experiences and memories that words can hardly capture. Cape Town was a vibrant and thrilling city, full of upscale shopping and exceptional dining. Jock Lodge stood out with its charming, rust..."

Christine Zastrow, United States•14 Oct 2025•

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