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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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"We live in Australia and I honestly didn’t know who to contact about organising a trip of a lifetime and I really wanted someone that knew Africa and not someone that was from Australia and just guessed. I found Discover Africa on TikTok and got in touch..."

Natalie Flick, Australia29 Jun 2026

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"From the very beginning, Bianca was a wonderful help in planning our South African safari. Her knowledge, attention to detail, and thoughtful recommendations made our trip truly exceptional. Becks Safari Lodge was, in our group’s opinion, a six-star expe..."

Leanne Morris, Australia12 Jun 2026

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"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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"I had a great trip organised by Chrizaan. Everything went very smoothly including all of the pickups, flights and accommodation. I visited Namibia and loved seeing the dunes, springboks and oryx. I also visited the Okavango Delta and saw so many anim..."

Leanne Harrison, South Africa03 Feb 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 States05 Jan 2026

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"I booked a three-day safari through Discover Africa, including flights, and everything went smoothly from start to finish. Communication was clear, timely, and genuinely helpful, making the whole trip easy and worry-free. The safari itself was exceptiona..."

Daniel, Sweden13 Oct 2025

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