To experience South Africa’s most spectacular cycling terrain, from dramatic coastlines to world-class vineyards, the Western Cape delivers it all.
The Western Cape of South Africa offers some of the world’s most dramatic cycling terrain, where the meeting of two oceans has carved a spectacular coastline that serves as a stunning backdrop for this relaxing cycling holiday. Here, beneath the iconic silhouette of Table Mountain, lies a landscape that seamlessly blends wild Atlantic coastlines with rolling vineyard valleys. A cyclist’s paradise that showcases the very best of what this remarkable country has to offer.
We’ve crafted our new South African adventure to capture the essence of this extraordinary region, taking cyclists from penguin colonies to world-class wine estates across eight unforgettable days of riding.
Our co-founder Andrew Straw (Straws) worked closely with our trusted local South African team to research and test every kilometer of this route. “The Cape Peninsula and surrounding wine regions offer cycling experiences you simply can’t find anywhere else in the world,” he notes. “You have this incredible contrast – one day you’re riding along dramatic coastal cliffs with cool Atlantic winds, the next you’re rolling through some of the world’s most beautiful vineyard country.”
Where Two Oceans Meet
The Western Cape is where the Indian and Atlantic oceans converge, creating a unique microclimate and ecosystem that cyclists experience firsthand. Starting in the Cape Penninsula in the historic naval town of Simon’s Town with its Victorian architecture, our route immediately showcases South Africa’s natural wonders with a mandatory stop at Boulder Beach penguin colony – one of the few places in the world where you can cycle within meters of wild African penguins.
The real character of the Western Cape reveals itself along the coast at places like Misty Cliffs, where the Atlantic crashes against dramatic rocky outcrops. The winds can be fierce at times but the views reward every pedal stroke. Then there’s the legendary Chapman’s Peak Drive – that iconic climb of the Cape Town Cycle Tour that features on every South African cycling bucket list.
“We want to give you plenty of opportunity to enjoy the views,” Straws notes. “The approach to Camps Bay with the Twelve Apostles mountain range looming overhead is genuinely breathtaking. We’ve ridden this section dozens of times and it still gives us goosebumps. When you finish beneath Table Mountain itself, you truly grasp the scale and beauty of Cape Town.”
Coastal Masterpiece
Moving beyond Cape Town, the route follows what’s often compared to California’s Highway 1 along Clarence Drive, though we think South Africa’s version is even better. Betty’s Bay offers more than just the Stony Point penguin colony; it has this wonderfully peaceful, end-of-the-world feeling that epitomizes the remote beauty of the South African coast.
The contrast between wild coastlines and manicured landscapes becomes apparent as you transition from dramatic ocean views to places like Arabella Golf Estate, perfectly encapsulating South Africa’s diverse beauty in a single day’s ride.
Into Wine Country
The true magic of this route lies in its progression from coastal drama to the pastoral charm of South Africa’s wine regions. The Elgin Valley, famous for its vineyards, apple orchards, and pear plantations, provides the perfect introduction to the country’s agricultural heart. Here, the transition from tar to gravel happens gradually, giving riders time to adjust while soaking in pastoral scenery framed by mountain backdrops.
“We couldn’t resist including some cheeky champers tastings and wine lunches along the way,” laughs Straws. “What’s better than bubbles after a morning’s ride through some of the world’s most beautiful vineyard country?”
The rolling hills of wine country showcase South Africa’s agricultural diversity. In early season, the vibrant yellow of rape seed in bloom creates stunning natural carpets across the landscape. Small towns like Greyton pulse with that unmistakable outdoor enthusiast energy, filled with bikers and hikers who gather at local establishments like the Old Potter’s Inn & Brewhouse for craft beer and conversation.
Valley Spectacular and Mountain Passes
The Hemel-en-Aarde Valley delivers some of the route’s most Instagram-worthy moments, with descents through wine estates offering photo opportunities every few kilometers. The ride concludes at a local brewery where cyclists can celebrate their achievements with well-earned craft ales, often while watching whales from the coast during breeding season.
But it’s the mountain passes that truly define this adventure. Franschhoek Pass represents the route’s “Queen Stage” – a legendary climb through 900 meters of elevation that’s beautifully graded so you can settle into a rhythm. “Cresting Franschhoek Pass reveals the valley below in all its ‘French Corner’ glory,” notes Straws. “We found ourselves sitting at the overlook in the sun, having a snack and soaking in views over Franschhoek and the surrounding wineries.”
Recce Highlights
During our reconnaissance trips, certain moments stood out as experiences we knew cyclists would treasure. The descent into Hout Bay after conquering Chapman’s Peak is absolutely thrilling. The approach through Ida’s Valley into historic Stellenbosch after cresting Helshgoote Pass provides the perfect conclusion to eight days of adventure, with the town’s Cape Dutch architecture and vibrant atmosphere creating an ideal backdrop for celebration.
“Creating this itinerary meant balancing challenge with reward,” explains Straws. “Each day needed to offer something unique while maintaining logical progression. From penguin encounters to world-class wine estates, from coastal dramas to mountain passes, this route showcases why South Africa deserves a place on every cyclist’s bucket list.”
A Taste of South Africa
The Western Cape’s culinary scene perfectly complements the cycling experience. Local wine estates offer not just tastings but full lunch experiences where cyclists can properly unwind and savor both vintages and the sense of having earned every sip. The region’s restaurants showcase fresh seafood from both oceans alongside locally grown produce and world-renowned wines from estates you’ve cycled past during the day.
We stop at small local establishments, farm stalls, and wine farms owned by and employing locals along the routes. The hospitality here is legendary – you’ll find warm welcomes and genuine pride in sharing what makes this region so special.
South Africa at Its Best
This is South Africa’s Western Cape at its finest. Where dramatic coastlines meet rolling vineyard valleys, where mountain passes challenge your legs and where every turn reveals another postcard-perfect vista. The result is a journey that creates memories lasting long after the bike is packed away.
“It’s been too long since we’ve launched another southern African adventure,” adds Straws enthusiastically. “This region offers everything we look for in a Skedaddle trip – incredible scenery, welcoming local people, fantastic food and wine, and cycling terrain that ranges from gentle vineyard rolling to a cheeky mountain pass thrown in here or there.”
Join us!
Read more about our South Africa cycling adventure and sign up for one of our upcoming trips!
South Africa – Western Cape