You’ll leave for South Africa from your chosen departure airports to Cape Town International Airport (CPT), generally arriving the next day.

• Meals: Dinner

Following our arrival at Cape Town International Airport (CPT) we are met at arrivals and transferred as a group to our hotel by the harbour and close to the V&A Waterfront in Cape Town. There are lots of flight options into Cape Town and for those not arriving for the group transfer we would suggest taking flight options that arrive by 3pm in order to get checked in before the group meal this evening. Once settled, we head out to enjoy a welcome dinner, meet our guides and the rest of the group, as well as be treated to a culinary introduction to the African continent.

• Meals: Breakfast, dinner
• Ascent: 580 Metres Approx.

After breakfast we transfer out to Boulder’s Beach in Simon’s Town. Home to a colony of endangered African penguins, our first stop of the day is the short walk along the public boardwalk to see these comical creatures while our bikes are unloaded and set up for the ride, fitting pedals and saddles for those who brought along their own.

The coastal ride from Boulders Beach in Simon’s Town to Hout Bay is one of the most scenic cycling routes on the Cape Peninsula. Leaving the penguin colony at Boulders, the road hugs the shoreline as it winds through quaint villages and rugged cliffs with uninterrupted views of False Bay. After the steady climb out of Simon’s Town (watching out for local baboons), the route rolls into Scarborough and Misty Cliffs, where we can pause at a local cafe for a well-earned coffee overlooking the wild Atlantic.

From here, the ride sweeps along the dramatic coastline, with Chapman’s Peak Drive offering breathtaking panoramas before descending into Hout Bay, where fishing boats, markets, and mountain backdrops provide a perfect finish to this leg of the journey.

• Meals: Breakfast, lunch
• Ascent: 540 Metres Approx.

We start the day with a boat trip to ‘Seal Island’ to see some of the thousands of Cape fur seals basking on the rocks of Duiker Island and playing in the surrounding waters. From the boat, we get a taste of the dramatic coastal scenery to come, beginning with great views over Sentinel Mountain.

Back on dry land, our ride today begins with a steady climb out of Hout Bay and up Suikerbossie, a legendary stretch for Cape Town cyclists, before dropping down into the Atlantic Seaboard with sweeping views of Llandudno and Camps Bay.

The coastal road carries us past palm-lined beaches and bustling cafes, before the gradient kicks up again as we turn onto Kloof Nek Road. The climb winds steadily between Lion’s Head and Table Mountain, with panoramic views of the city bowl unfolding as we gain altitude. At the crest we have the imposing cliffs of Table Mountain towering above and we can reward our efforts with a well-deserved picnic at the base of the Cable Car station, surrounded by fynbos and spectacular city and ocean vistas – the perfect finale to a classic Cape Town cycling adventure.

We’ll watch the weather and if the cable car is running we have the option to take the short journey up to the top of Table Mountain for great views over Cape Town and the surrounding bay. We stay back in Cape Town tonight with plenty of local options to choose from for our evening meal.

• Meals: Breakfast, lunch
• Ascent: 470 Metres Approx.

To avoid the city traffic we take a transfer out of Cape Town this morning and head to the far side of False Bay and the delightful coastal town of Gordon’s Bay. Starting from the picturesque harbour, the ride traces the famous Clarence Drive, a coastal road carved into the mountainside that offers uninterrupted views over False Bay and the rugged shoreline below.

The road twists and turns through dramatic cliffs, with whales often spotted in season, before easing into the laid-back seaside town of Pringle Bay. Here, a stop for fish and chips by the beach makes for the perfect lunch stop.

From Pringle Bay, the route bends inland, rolling past wetlands and mountain vistas. The smooth, winding roads will lead us through the quiet town of Betty’s Bay, home to the famous Stony Point penguin colony and as we head past Kleinmond into the wetlands we may see some of the resident wild horses which roam and graze between the wetlands and the coastal dunes.

Our final kilometres of the day take us to the luxurious Arabella Hotel. Tucked beside the Bot River Lagoon and surrounded by pristine fynbos, Arabella provides a tranquil and indulgent finish – the ideal reward after a ride through one of the Cape’s most beautiful coastal stretches.

• Meals: Breakfast, lunch
• Ascent: 650 Metres Approx.

Leaving the Arabella Hotel, the ride quickly heads inland towards Highlands Road, a cyclist’s gem that winds through rolling vineyards, apple orchards, and mountain backdrops. We start with a steep climb on compact gravel on a road that is quiet, shaded in parts, and offers breathtaking views over the Elgin Valley. The majority of today’s riding will be along quiet compacted gravel roads.

Midway along, we’ll stop at Charles Fox for a tasting of their renowned Methode Cap Classique – crisp, elegant bubbles that are the hallmark of this boutique estate. Energised, the ride continues deeper into cool-climate wine country, with the route flanked by lush vineyards and orchards.

The final stretch takes us to South Hill Vineyards, a welcoming estate where art, wine, and hospitality converge, making it a perfect ending point to relax and soak in the serene Elgin landscape after a rewarding ride. While we enjoy a relaxing lunch our bikes will be loaded on the trailer ready for the 20km transfer to our hotel in Houw Hoek which allows us time to relax and avoid a short stretch along a busy road.

• Meals: Breakfast, lunch
• Ascent: 600 Metres Approx.

Setting out from Rooiheuwel Farm just outside Botrivier, our ride begins on rustic farm tracks rolling alongside the old railway line, giving a sense of the valley’s history and rhythm. The gravel roads undulate gently, framed by wide farmlands, grazing livestock, and the looming mountains in the distance.

During our ride we’ll keep an eye out for the majestic Blue Cranes, South Africa’s national bird which are now on the vulnerable list yet thrive in the agricultural fields of the area. This stretch offers a quiet, backcountry feel with few cars, making it perfect for soaking up the raw Overberg landscapes.

Continuing on, the route sweeps towards Greyton, one of the Western Cape’s most charming country towns. The final approach rolls through orchards and open fields before we arrive at Greyton’s leafy streets, where quaint cottages, coffee shops, and mountain views provide a rewarding and relaxed finish to the ride.

• Meals: Breakfast, lunch
• Ascent: 440 Metres Approx.

We start today with a transfer to the town of Caledon where we will begin our ride and where there’s great local coffee on hand if we need a boost as we unload the bikes.

Rolling out of Caledon, our route follows the tar road that threads through the wide, open countryside of the Overberg. Golden wheat fields and distant mountain ranges frame the ride, with long, gradual drags testing the legs before rewarding sweeping downhills. The scenery steadily shifts as we approach the Hemel-en-Aarde Valley – its name translating to ‘Heaven and Earth’ – a fitting description for this spectacular landscape where the mountains meet the sea. Lush vineyards and cool-climate terroir signal our arrival into wine country, and the road winds gently through this celebrated valley until we reach the edge of Hermanus. Here we set the bikes down to indulge in some local produce, with a local brewery and restaurant next door to one of South Africa’s largest wine stores there is something for everyone.

Between August and October each year the sheltered Walker Bay attracts large numbers of southern right whales which come to the bay to mate and calve. Here, the huge mammals come very close to the rocky shore to feed and breach and Hermanus is considered to be one of the world’s best land-based whale watching destinations. We’ll check into our accommodation later this afternoon and have some free time to enjoy the sea views, coastal paths and sculpture trails around Gearings Point.

• Meals: Breakfast, lunch, dinner
• Ascent: 740 Metres Approx.

Ready to take on our biggest day of the trip, we start with a short transfer to Goedvertrouw Farm. Our ride begins gently at first on the quiet unsurfaced country tracks of Van der Stel’s Pass and is framed by vineyards, orchards, and the rugged slopes of the Houwhoek Mountains. The pass itself rolls gently, offering sweeping views of the valley before dropping us down towards the Theewaterskloof Dam. Here, the vast expanse of water reflects the surrounding peaks, and the road hugs the shoreline for a truly scenic stretch.

From the dam, the route climbs steadily into the Franschhoek Valley, renowned for its vineyards and Cape Dutch heritage. The final challenge is the iconic Franschhoek Pass where the scenery invites us to take our time on this legendary ascent with its hairpin bends and breathtaking panoramas across the valley and dam below. Cresting the pass at the entrance to the Mont Rochelle Nature Reserve, we pause to take in the amazing views of Franschhoek set amidst gorgeous scenery in the valley below.

Back on the bikes, a winding descent delivers us into Franschhoek town, where cafes, wine estates, and mountain vistas make for a world-class finish to this epic ride. We’ll head into town tonight to eat together and indulge in a fitting celebration for today’s challenge.

• Meals: Breakfast, lunch
• Ascent: 290 Metres Approx.

Leaving Franschhoek, our route avoids the busier main road by detouring onto the scenic unsurfaced Robertsvlei Road. This quiet stretch winds through vineyards and farmland, with the dramatic Drakenstein Mountains as a backdrop, before curving towards the Berg River Dam, a serene body of water tucked among fynbos-clad hills.

From here, the route turns towards the Helshoogte Pass, one of the Cape’s classic climbs, where vineyards line the road and oak trees give dappled shade along the ascent. The old road is now only accessible to walkers and cyclists and we can enjoy the delightful scenery on this traffic-free route to Stellenbosch. At the top, we can pause at Tokara Wine Estate (or one of its neighbours) to enjoy sweeping views over the Stellenbosch Valley and perhaps a well-earned coffee or glass of wine. The ride then continues down the old Helshoogte pass through Ida’s Valley, a quiet, tree-lined route that offers a gentle and historic descent.

Rolling into the centre of Stellenbosch on the purpose built cycle path, today’s ride finishes amid leafy avenues, heritage architecture, and the vibrant cafe culture of South Africa’s wine capital, the perfect place to celebrate the last evening of our trip.

• Meals: Breakfast

A relaxed final morning in lovely Stellenbosch, with the opportunity for last purchases and time to pack our bags, before a group transfer to Cape Town later this afternoon.

For those wanting to stay on in the Western Cape, there are plenty more options to fill your schedule, with Cape Town being a fantastic base for day trips to Robben Island, Kirstenbosch Botanical Gardens and countless wineries and spas if you are looking to indulge in some relaxing days. For those looking to explore a different side of South Africa, then chat to our team about Kruger safari extensions which we can arrange from Johannesburg.