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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

"This was our first experience using an online booking agent and it was outstanding. Justin went through our requirements even though we were pretty sure we knew what we wanted (we really didn't!) and came up with a plan that met our needs, including coordin..."

John Colao, United States13 Apr 2026

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Safari Bookings review

"After discovering a high number of camps in and around the Okavango, and at a price higher than we typically go for on a safari, we were very unsure on the route to go down for our honeymoon (especially whilst trying to planning our wedding!). So we reached..."

Rhys and Grace Fitzgerald, Bahrain10 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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Google review

"I was very pleased with the information, help and booking process provided by Cayleigh"

David Partridge, United Kingdom16 Mar 2026

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"We had a truly magical safari experience perfectly planned & organised for us by Susan Veldman at Discover Africa. We flew from Cape Town to Hoedspruit and then seamlessly transferred to the most beautiful lodge in the Karongwe private game reserve. ..."

David Forbes, United Kingdom03 Feb 2026

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"I was recommended Discover Africa by a friend who raved about them for their African Safari adventure and they didn't disappoint. From the start the communication was timely, despite the time zone difference, and the advice was thorough and precise. It seem..."

Stephen Suster, Australia18 Jan 2026

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