A ride in South Africa is more than a bit of exercise. It’s a ride through a long and troubled history and into a bright future, through the ever-changing terrain of cityscapes, towering mountains, heritage vineyards, nature reserves, and along winding coastal roads that look across fierce cliffs. From Cape Town, head into the country's famous winelands and savour scenic passes and local wines on the way to historic Stellenbosch. Cross nature reserves and twist through the Langeberg mountain range down to the continent’s southernmost point. Squeeze between mountain peaks, look out for whales in Hermanus, hug the edges of the Kogelberg Nature Reserve, then explore the tracks of Cape Peninsula. Return to Cape Town with memories of a lifetime.


Active Adventures


We think the world’s at its best when there’s nothing between it and you. No big bus window. No iPhone screen. No maps or walls or guidebooks. Just the wind and the open road.
  • Highlights

    • Cycle in the shadow of the majestic Table Mountain, with the blue waters of the Atlantic Ocean a constant companion by your side
    • Encounter the ‘real South Africa’ while cycling across the rural landscape dotted with small historic homesteads and towns
    • Get to know the two finest mountain passes in South Africa on two wheels, then be rewarded with thrilling freewheel downhill rides
    • Stand on Cape L'Agulhas – the southernmost point in Africa, where the Indian and Atlantic Oceans meet, and enjoy unobstructed views towards Antarctica
    • Swap water bottles for wine bottles at the famous vineyards of Stellenbosch and beyond, refuelling with South African delicacies
  • What's Included


    9 Breakfasts, 8 Lunches, 8 Dinners


    Bicycle (e-bike option available , subject to availability) , Support Vehicle


    Hotel (7 nights), apartment (2 nights), chalet (1 night), cottage (1 night)

    Included Activities

    • Birkenhead Brewery
    • Cape Peninsula - Boulders Beach Penguin Colony
    • Cape Peninsula - Day Tour
    • Fairview Wine Estate - Wine tasting and Cheese Pairing
    • Route 62 Wine Tasting
    • Stellenbosch Full Day Cycle
  • Pricing

      • Start Date
      • End Date
      • Price
      • Availability
    Please note: while prices are accurate at time of loading they are subject to change due to currency fluctuations and currency surcharges may apply. Please check price at time of booking
  • Itinerary

    Day - 1

    Location: Cape Town - Sawubona! Welcome to South Africa. Your hotel is perfectly located between Signal Hill and the majestic Table Mountain. There are no activities planned today until an important group meeting at 6pm – double check with reception for the time and place. If you can't arrange a flight that will arrive in time, you may wish to arrive a day early. We'll be happy to book additional accommodation for you (subject to availability). If you're going to be late, please inform the hotel reception. Insurance details and next of kin information will be collected at this meeting, so please have these on hand. As there’s not much time spent in Cape Town on this trip you may wish to arrive early into this scenic city. With its stunning coastline, dramatic surrounding mountains and modern cityscape, Cape Town is one of Africa's most appealing cities and a great place to start your trip. The infamous Robben Island (Nelson Mandela’s prison for 18 years), vineyards, adventure activities and plenty of good restaurants and cafes are all at your doorstep. After the meeting tonight, maybe walk to nearby Long and Kloof streets for great nightlife. Riding distance: None


    Day - 2

    Location: Stellenbosch - Meet your bike support team, get fitted to your bike, then take a quick ride to make sure everything’s working. Leave beautiful Cape Town on four wheels to begin with, driving to Blouberg to see the iconic Table Mountain – don’t forget your camera! Soak in the incredible view, then continue east towards the winegrowing region of Paarl and the famous Fairview property. While Fairview has been producing wine since 1699, you’ll be sampling some of their later vintages on an included wine and cheese tasting. The epicurean experience continues with a stop at the iconic Spice Route at Seidelberg Wine Estate. The old farmhouse offers an assortment of typical South African delicacies, including local wines, barley beer, biltong, and artisan chocolates – perfect for an optional lunch. This afternoon, work off a few of those calories with a cycle, starting in the outskirts of nearby Wellington. Climb the dozens of hairpin turns on one of South Africa’s finest scenic passes – Bain’s Kloof Pass. While it’s a stiff uphill ride for the first half, the views are spectacular and there’s the pleasure of an all-downhill second half on a sealed road to the Breede River (approximately 30 kilometres). After this enjoyable ride, climb back into the vehicle and drive west to the ‘City of Oaks’, the graceful town of Stellenbosch. Riding distance: Approx. 30kms Notes: Cape Town to Wellington is approximately a 95-kilometre drive, with Breede River to Stellembosch approximately 90-kilometres.


    Day - 3

    Location: Stellenbosch - Today is back on the bike but for a different type of ride. It’s a fairly relaxed affair as you experience a full day cycle and wine tasting tour (10am-4pm, covering around 20 kilometres). Enjoy tastings at three superb wineries, with a focus on the smaller, boutique wineries of the Stellenbosch region. The cycling route takes you along private farm roads, through the breathtaking vineyards, quiet tree-lined roads and spectacular mountain views of the area, before returning to Stellenbosch itself. Back in town, you’ll have a free afternoon and evening to explore its leafy cobbled lanes and elegant mix of 18th century architecture. This evening, why not head out to AmaZink Live, South Africa’s first township theatre restaurant, or for something completely different try the Stellenbosch Ghost Tour, a spooky introduction to South Africa’s second oldest town. Riding distance: Approx. 20kms


    Day - 4

    Location: Little Karoo - This morning, climb back into the vehicle and begin the long but scenic journey east through the Haweqwa Nature Reserve. There are few better ways to break up a drive than with stops at several wineries – so that’s exactly what you’ll do. Continue on to meet the scenic Cape Route 62 at the historic spa town of Montagu (approximately 160 kilometres). After a long drive, get out of the vehicle and stretch your legs on a cycle that heads gradually uphill, following alongside the Marloth Nature Reserve. You’ll be surrounded by some striking mountain scenery and the semi-desert region of the Little Karoo – the treeless plains and smooth topped hills a severe but beautiful backdrop for this 65-kilometre ride. Tonight you’ll stay in Barrydale, a small rural town that lies at the foot of the towering Langeberg Mountain Range in the heart of the fertile Tradouw Valley – a sharp contrast to the starkness of Little Karoo. Riding distance: Approx. 65kms


    Day - 5

    Location: Bontebok National Park - Tackle one of the best rides of the whole trip today, with the climb over the Tradouw Pass twisting through some of the most beautiful and rugged mountain scenery in the Langeberg. The climb itself isn’t actually too hard as you gain less than 300 metres of elevation, and the stunning backdrop and smooth sealed road will help you forget the ache in your legs (approximately 35 kilometres). There are several areas to stop and admire the spectacular views down into the gorge of the Buffelsjags River, with its onyx-coloured rock pools and waterfalls. Travel along the reverse side of the Zuuberg Nature Reserve, then climb back into the vehicle to avoid the busy truck traffic on the N2 highway and drive through Swellendam. Continue on the short distance to Bontebok National Park (approximately 20 kilometres), the smallest National Park in South Africa. Lying on the banks of the Breede River, this park is built to protect the endangered Bontebok (a native antelope) and has a variety of safe trails perfectly suited for cycling. When you arrive you can choose to cycle a few more kilometres to check out the park, or simply relax at camp with a cold drink and a beautiful view – the choice is yours! Riding distance: Approx. 35kms


    Day - 6

    Location: Cape L'Agulhas/Arniston - Leave the inland behind and head south to Cape A'gulhas (“Cape of the Needles”), the southernmost point in Africa where the Indian and Atlantic Oceans meet (approximately 140 kilometres). The sea off Cape Agulhas is infamous for winter storms and huge rogue waves, resulting in the sinking of around 150 ships over the centuries. Start your cycling for the day here after an optional visit to the Cape A'gulhas Light House. Ride along the flat rural roads (a mixture of sealed and unsealed), curving east and then hugging the rugged coastline until you reach the small seaside town of Arniston (approximately 45 kilometres). Famous for its whitewashed thatched cottages that line the shore, this fishing village remains unchanged over the years. It’s a great place to simply relax and take in the amazing ocean views after a long day’s cycling. For a change of pace, maybe take an easy stroll to the impressive Waenhuiskrans Cave. This beautiful sea cave can only be reached at low tide and is huge. Its name means ‘wagon-house cliff’ because it’s thought to be big enough to hold a wagon and a full team of oxen (not that you could actually get your oxen or cart down here).  Riding distance: Approx. 45kms


    Day - 7

    Location: Hermanus - Today is a long travel day and so there will be two separate rides. Leave sleepy Arniston behind and make the short vehicle transfer to nearby Bredasdorp (approximately 25 kilometres). Here you’ll jump back on the bikes and cycle the rolling route along smooth tarmac through classic South African farmland, up to the delightfully rural town of Napier (approximately 20 kilometres). As the road gets busier from here you’ll reboard the vehicle and transfer to the base of the famous Akkedisberg Pass (approximately 30 kilometres). While now topped with a smooth sealed road, the original gravel road dates back to 1776 and is one of oldest passes in South Africa. There are some steep sections but the pass itself rises less than 100 metres. Your climbing is quickly rewarded with a thrilling downhill ride that follows the path of the Klein River all the way down to Stanford. Here you’ll visit the Birkenhead microbrewery and be rewarded with a cool lager or wine in the shadow of the Klein Rivier mountains. After this short refreshment break continue west, through the dramatic scenery where the rugged mountains meet the Klein River lagoon, until you finally hit the ocean at the beautiful town of Hermanus (approximately 45 kilometres). The self-catered apartments here will be your base for the next two nights. Notes: The road from Stanford to Hermanus can occasionally get very busy with traffic – should your leader feel there is a safety risk on the day we will drive this section instead. Riding distance: Approx. 65kms


    Day - 8

    Location: Hermanus - Today is a free day for you to enjoy all that Hermanus has to offer. The town is renowned for being an excellent destination for whale watching, and is considered to have the best land-based whale watching in the world. You could try the Whale Walking tour with the Hermanus Whale Crier or, if you are desperately missing your cycling crowd from back home, join the Hermanus Cycling Club on their regular Saturday ride. You are welcome to explore the area on bikes at any time. The town also has a variety of adventure activities on offer, beautiful award-winning beaches to relax on, and abundant hiking trails in nearby Femkloof Nature Reserve. For something less active, there are fantastic markets and excellent cuisine on offer too. Riding distance: None


    Day - 9

    Location: Gordon's Bay/Simonstown - Another spectacular ride lies in store today as you cycle the coastal road through Betty’s Bay all the way to the harbour town of Gordon's Bay (approximately 70 kilometres). With the dramatic peaks of the Kogelberg and Steenbras Nature Reserves on the right, and endless beaches and ocean views on the left, this is a truly stunning ride. From here you will continue by vehicle, passing beneath the imposing Helderberg Mountain before returning to the beach road and on to Simon’s Town (approximately 85 kilometres). This is the home of the South African Navy and the gateway to the stunning Cape Peninsula. Evidence of a 200-year naval history is all around you but is best seen in the 1795 British-built Martello Tower near the naval base. Simon’s Town is also home to a beautiful beach with a spectacular mountain backdrop, as well as a nearby penguin colony. Please note we sleep the night in Cape Town. Riding distance: Approx. 70kms


    Day - 10

    Location: Cape Peninsula - Today you’ll experience a close-up encounter with nature at the nearby Boulders Beach Penguin Colony, home to a colony of vulnerable jackass penguins nestled among the giant granite boulders. Here you can view these cute little fellas at close range as they wander freely in their natural environment. Later in the day, drive the dramatic coastal road south through the Table Mountain National Park to explore beautiful Cape Peninsula, visiting Cape Point and the nearby Cape of Good Hope. Retracing your steps, cycle back to Simon’s Town, enjoying the downhill sections of this picturesque route (approximately 35 kilometres). The rest of the day is free to enjoy Simon’s Town’s ample activities before we return to Cape Town – why not join a boat cruise to Seal Island, home to 75,000 Cape Fur Seals, 24 different bird species and a favoured hunting ground of the Great White Shark. If you feel like just kicking back, there’s always Long Beach or the vast array of spectacular outdoor eating locations. Please note we sleep the night in Cape Town. Riding Distance: Approx. 35kms


    Day - 11

    Location: Cape Town - The very best ride has been saved for today, your final day on the bike. Cycling part of the prestigious Cape Argus cycle route, follow the hilly west coast of Cape Peninsula through numerous seaside towns, past beautiful beaches and, of course, beneath the legendary Table Mountain itself. There’s no denying that today’s ride is a tough one – it involves over 1,300m of climbing in 65 kilometres, and the hills start early as you begin to climb the hairpins of the Peninsula. As soon as you hit the top of the escarpment it’s a nice 8-kilometre downhill to the west coast, then across the undulating (sealed) coastal road from there. For those feeling tired, or who’d simply prefer to enjoy the scenery from the comfort of the support vehicle, it’s there at your disposal – but we really recommend trying to cycle as much of this route as possible. Your ride ends at the famous red and white striped Green Point Lighthouse, close to the centre of Cape Town itself. Get back into the vehicle to avoid Cape Town’s chaotic traffic and take a short five kilometre transfer to your hotel. There’s plenty of time to get cleaned up and perhaps go out for a final celebratory dinner with your fellow cyclists. Riding Distance: Approx. 65kms


    Day - 12

    Location: Cape Town - This memorable cycling adventure through South Africa comes to an end today. There are no activities planned and you are free to depart at any time. If you wish to stay on in Cape Town additional accommodation can be arranged – please enquire at time of booking. Riding distance: None


    Cycle Cape Town & Winelands
*Terms and Conditions
Offer subject to availability at time of booking. Prices are per person share twin based on best available tour price, inclusive of all discounts unless otherwise stated. Prices are subject to currency fluctuations and are based on cash or cheque. Tour deposit, amendment and cancellation conditions may apply. Travel agent service fees may apply. Special conditions apply - please ask for full details at time of enquiry.
HLO Ref# 9681
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