I had been curious about South Africa for a long time. Growing up, I learned about Apartheid and Nelson Mandela, as part of history class in school. Over the years, I picked up little details about current events in the country here and there. It very much entered my consciousness again when hosting the Soccer World Cup in 2010, the sounds of the vuvuzelas still ringing in my ears. Now I had the unique chance to travel there myself and was eager to learn more about this country first-hand, with its troubled yet rich history and the vibrancy in its culture.

After arriving in Cape Town, I decided to spend a few days exploring the city before boarding a Baz Bus, a hop-on/hop-off shuttle van service geared at backpackers. It was the only financially viable option to get me and my bike to Plettenberg Bay, the start of the Cross Cape cycling route. My Trek Checkpoint securely stowed in the trailer, it was a tedious ten-hour bus ride, the kinds I swore would never repeat any time soon. The plan was to ride the route from east to west, which should mostly put the wind in my back this time of year. So much about the theory.

I had departed Cape Town under blue skies and oppressive heat, but about 520km east, in “Plett”, as the locals call it, the weather conditions looked vastly different. Rain and wind greeted me upon arrival. As I cycled inland, heading into the Langkloof Mountains, the situation only seemed to get worse. The sand and gravel roads had suffered significantly from the downpours over the preceding days, with a never-ending parade of potholes, washboard sections, and drainage channels carved into the soft surface. Progress was slow and painful. The promised hilltop views of the lush green landscape remained primarily hidden behind veils of fog and mist.

As I was pedaling along to the crunching sound of the fine-grained wet sand on my drivetrain, I also encountered some wildlife. Cows were contentedly chewing on some grass by the wayside, whereas a troop of free-roaming monkeys scattered as soon as I approached. I envisioned them privately mocking my seemingly ridiculous efforts of being out cycling in this weather.

At the top of the crest, I turned south onto Prince Alfred’s Pass, a dirt road popular with motorbikes and 4WD vehicles. Navigating through the jungle-like atmosphere in Diepwalle Forest, the forest road slicing through what otherwise looked like impenetrable vegetation, thoughts of wild animal encounters spooked around in my head. Could I have a close encounter with one of the Big 5 in this area?

From the town of Knysna, I headed out to conquer the Seven Passes Road. Built between 1867 and 1882, it connects Knysna in the east with George in the west. As the name implies, the mostly hard-packed gravel road links up seven passes, which are, luckily, of relatively low elevation (250 meters (820 feet) range). Most of them share a similar characteristic by descending through a river gorge and climbing back up on the other side. The recent wet weather had certainly not done me any favors, requiring some grit to make it up those ascents on the sticky, damp sand. The corrugated surface turned many of the descents into teeth-clattering affairs.

Like so many mountain roads in South Africa, this, too, was constructed by the road engineer Thomas Charles John Bain. Between 1848 and 1888, he was responsible for planning and building over 900km of roads and mountain passes. These projects played a significant part in opening up the vast backcountry to economic development.

Montagu Pass was my gateway across the Outeniqua Mountains in the north. Opened in 1848, it had taken three years to build the pass and was the first construction project of its kind to mainly utilize convict labor. With little traffic and fog covering the upper slopes of the valley, it was a bit eerie cycling up the narrow, bendy gravel road. Dropping down the other side meant I had firmly left the moist and misty coastal region behind and entered the Klein Karoo (Afrikaans for “Little Karoo”). This region represented the southernmost part of the (Great) Karoo, an expansive semi-desert area in the country’s interior.

The climate and vegetation on the other side couldn’t have been more different from what I had experienced along the coast. Lush green foliage, grass, and shrubs had given way to knee-high, hardy bushes on bare and arid, wide-open space. Early adventurers and explorers “unanimously denounced it as a frightening place of great heat, great frosts, great floods, and great droughts.” On dry, dusty and corrugated dirt roads, I continued on over undulating terrain. Eventually, I made it to Oudtshoorn, home to the world’s largest ostrich population and several specialized breeding farms in the area.

Leaving Oudtshoorn and heading west, I started to feel quite a bit uneasy. By that point, I had heard way too many stories of muggings and robbery, some targeting tourists but also locals. I had to be vigilant at all times, trust my instincts, and decide whether an area looked safe to linger or if it was better to move on quickly. I probably erred on the side of caution most of the time, but the last thing I wanted was any of my gear forcibly removed from me. Needless to say, always being on high alert was mentally tiring.

Passing some tiny settlements and farms outside of town, I soon found myself climbing into the hills again on a wide dirt road. For the first part of the day, I very much steered head-on at the impressive Swartberg Mountain Range, whose upper slopes remained stubbornly hidden behind a layer of clouds and fog.

The higher I got, the more the vegetation seemed to change again, aided by large amounts of rain the area had seen recently. The fields of different kinds of succulent types next to the road were a testament to the Klein Karoo being home to one of the richest and most diverse habitats in the world for this category of plants.

Seemingly in the middle of nowhere, I reached a T junction, where I turned west. The long-awaited descent that followed took me past more farmland and, much to my excitement, required some stream crossings. I would find out later that those would have been impassable just a few days prior due to rainfall. At last, I made it to the town of Calitzdorp, pop. 4,284, renowned as a center of the port wine industry in South Africa.

The ride from Calitzdorp to the small hamlet of Van Wyksdorp was characterized by a rugged climb up to Rooiberg Pass and a series of technical mishaps. As I rode past vineyards and ostrich farms outside town, my rear (tubeless) tire seemed to lose air despite any visible leaks. Forced to switch to an inner tube, said tire gave out again shortly after reaching the pass. With no options left apart from tire patches that had lost their stickiness, I continued on a flat tire.

“No reception, of course,” I thought, staring at the zero-bar indicator on my phone. The area very much desolate and void of any settlements, I wasn’t sure if I would make it out of this desert before nightfall. I frankly was not keen on finding out about what animals were lurking in the shadows at night. I slid and skidded down the dirt road and then moved along with a combination of walking and rolling down gentle descents.

Luckily I managed to find a water source along the way to take care of hydration needs. Eventually, I managed to get a hold of Russell, the owner of Watermill Farm Cottages I had made a reservation at. He did not hesitate to offer to pick me up in his pickup truck roughly four miles outside of town. As much as I would have liked to complete the day under my own power, I was glad about getting a lift. Sometimes days really do not work out as planned.

Upon inspection of the situation, it turned out a new tire would be necessary. I took Russell up on his offer to give me a ride to Riversdale, roughly 60km away, and the town I had planned to reach next. Sadly this meant missing out on cycling up and over Garcias Pass and views of Sleeping Beauty Mountain. In Riversdale, I was lucky enough to find Riversdale Cycles (now closed, unfortunately), a quality bike shop run by Quewin and his brother Reece. With the confidence of a new tire, I was ready to continue on my journey the next day.

I took Quewin up on his suggestion to follow a slightly more laid-back route out of town, mostly a hard-packed dirt road, gently rolling through farmland. However, the rough surface did not deter the dozen or so drivers speeding along at 60 to 70 km/h, hurling tiny pieces of gravel my way. By noon I had made it to Heidelberg, where I stopped for a snack at a bakery and refilled my water bottles. The road changed from tarmac to gravel just outside of town, and I soon found myself laboring up yet another incline in the midday heat. A gripping downhill on the other side took me to Suurbrak and into the Overberg District Municipality. From there, it was another 13 miles into Swellendam, the final few on the shoulder of the N2, the country’s main highway, running parallel to the coast.

Swellendam boasts over 50 provincial heritage sights with most of the buildings constructed in Cape Dutch architecture style. What struck me was the much cleaner and more upscale appearance of the town, not unlike popular weekend getaway destinations for the middle and upper-middle class in the United States. Upon research, I found of note that the Swellendam Municipality area redeclared itself a Republic in 2011, dedicated to the principles of the New South Africa: celebrate rural life, racial harmony, respect for nature and wildlife, and aiming to promote sustainability and an “unplugged” way of life for all to enjoy.

I woke up early at my guesthouse in Swellendam, well-rested and, to my surprise, to vastly different weather conditions. While I had suffered through stifling heat the previous day, temperatures had dropped to about 15C (60F) and would not go much higher throughout the day. A rainy morning and wind were precursors of things to come. With the mountains of the Langeberg Range to my right, I cruised out of town, working against a steady headwind that would be my constant companion for the rest of the day. Like the previous morning, it was a ride over rolling hills, past countless farms, on mostly decent hard-packed gravel roads. At least at the beginning.

Throughout the day, I had to contend with varying weather conditions, frequently switching between a slight drizzle, full-on rain and headwinds steadily increasing in force. A dirt road I connected with after two-thirds of the day’s mileage behind me turned out to be the worst road I had cycled on thus far. It was littered with big rocks and potholes, sections filled with sand, and washboarded in irregular intervals. With the headwind kicking up, progress was frustratingly slow.

A handful of miles outside Riviersonderend—a village name I was never able to pronounce correctly—I finally connected back to the N2. I arrived in the small town late afternoon with just enough time for a coffee and a pastry at Ou Meul Bakkery. In addition to delicious baked goods, the bakery also carries a wide range of local products, including olive oil and honey and coffee beans from Bootlegger Coffee, a South African coffee company.

Heading out of Riviersonderend on the N2 highway the following day, I turned onto a gravel road fairly soon, riding past dairy farms and fruit orchards. The views of the Langeberg Range to my right were awe-inspiring, and luckily the wind had calmed down from the day before. After three hours of riding, I reached the charming town of Greyton, perfect for a coffee stop. The route followed the Sonderend River’s path, which made for mostly pleasant riding without a lot of elevation changes. From the top of Floorshoogte Pass, a gripping downhill on the other side took me past Theewaterskloof Dam, the largest dam in the Western Cape Water Supply System and a crucial water source for Cape Town. I ended the day in the town of Villiersdorp in the Cape Overberg Region, an area known for producing apples, grapes, onions, peaches, and apricots.

Turning away from Theewaterskloof Dam, the traffic luckily quieted down on the flat tarmac road leading up to the 7km climb to the Franschhoek Pass summit. Past the grass and bushland around me, vistas of the Mont Rochelle Nature Reserve on my right, as well as extensions of the Hottentots Holland Mountains on the left. The grade of the climb wasn’t too intimidating, but high temperatures made it tough going in parts. The impressive views served as a welcoming distraction on the way up.

From the top of the pass, I dropped down into the town of Franschhoek (Afrikaans for “French Corner”). Once a sleepy country retreat, the community experienced a boom in the 1990s, with property prices sharply rising. Today the area prides itself on housing roughly 50 wineries, numerous top restaurants, and well-preserved original Cape Dutch architecture and natural beauty throughout the valley. It very much reminded me of towns in Napa Valley, the San Francisco Bay Area wine region.

“Very little was here in the Eighties,” James, a local running his own carpentry business, tells me. We started talking after I had stopped for coffee at The Hoek Espresso Bar, along the main street. Growing up here, he remembers playing tennis with friends on the road, so little car traffic was coming through. “Things opened up after Apartheid ended and really took off in the 2010s.” According to him, lots of foreigners started buying up farms in the area, converting them into estates/gated communities.

After a brief detour to Berg River Dam, I continued on R45, cycling past countless wineries on my way west. On a couple of occasions, I found myself riding behind a wine tour bus, shuttling enthusiasts from one wine tasting venue to the next. Catching my breath after the final climb up Helshoogte Pass, all was left to do was cruise down the other side and into Stellenbosch, my destination.

The thrill-inducing descent was the appropriate conclusion to this journey. I zoomed through residential neighborhoods before reaching the downtown area of this college town, home to Stellenbosch University. I celebrated, quietly and by myself, with a coffee and a pastry from Blue Crane Coffee Company. There was definitely a lot more to explore in South Africa, but I was content with my glimpse into the landscape, culture, history, and people of the Western Cape, made possible by the power of a bicycle.

For this tour I decided to follow the Cross Cape, a cycling route ascross South Africa’s Western Cape region, starting in Plettenberg Bay and ending in Stellenbosch.

The path takes you through some iconic landscapes in the region along the Garden Route, Klein Karoo, Cape Overberg, and Cape Winelands. With the time I had given myself, I thought this would be a great way to sample and experience this part of the country.

A good alternative to this could be the Western Cape Passes Epic from BIKEPACKING.COM, starting in Barrydale and ending in Jeffrey’s Bay.

After some research, I decided to ride the route from east to west (rather than west to east) due to the expected prevailing wind direction this time of year.

This meant flying into Cape Town International Airport and using Cape Town as the base for my trip. If you have reservations for both at the beginning and end of your trip, hotels usually are happy to hold on to any luggage items until your return.

To get to Plettenberg Bay, the starting point of the route, I made a reservation with Baz Bus, a hop-on/hop-off shuttle bus service geared towards backpackers, running from Cape Town to Johannesburg. They use a sizeable trailer for luggage, which is also big enough to transport bikes. You might not even have to take any wheels off for the journey.

I planned my daily mileage so I could end up in a town at the end of each day. This meant an opportunity to stock up on supplies, as those usually have at least one grocery store. Because I was familiar with the brand from Europe, I prefered shopping at a SPAR store.

Drinking water is often a bit more harder to come by, especially after entering the Klein Karoo. It is advisable to carry enough water containers and refill whenever possible in those areas.

If you like to stock up a bit before leaving Cape Town, there are several Cape Union Mart locations throughout the city, most notably two at the V&A Waterfront. Here you should be able to obtain any last-minute hiking and general outdoor items. Additionally, there are a handful of bike shops in the Sea Point/Green Point neighborhoods, however I did not have a need to visit them before departure so can’t necessarily speak to their quality of service.

Under more favorable conditions, a gravel bike with wider tires would be the ideal bike for this route, since the majority is on hard gravel and dirt roads, with the rest on tarmac. The heavy rain the area had experienced prior to my arrival, however, had turned plenty of the roads into washboarded sections. Overall, a mountain bike with front suspension and plus-sized tires would definitely provide more comfort, but might be overkill taking the full length of the route into account.