Your itinerary
Day 1
Adventure begins in Cape Town
Begin your adventure in cosmopolitan Cape Town, undeniably beautiful, culturally rich and a gateway to world-leading vineyards.
Around 5pm, say howzit to your tour leader and fellow travellers, when we gather as a group for the first time to get to know each other and learn more about the adventures ahead.
Your tour leader then ensures a big South African welcome by arranging dinner at a local restaurant.
Want to explore Cape Town further? Secure pre-tour hotel nights through your sales representative.
Meals: Dinner
Day 2
Ride along the Cape Peninsula to either Stellenbosch or Franschhoek
Ride from Hout Bay along the Atlantic edge, following Chapman’s Peak Drive, an early-20th-century feat of engineering cut directly into sheer coastal cliffs. Guided by our tour leader, we trace the natural curves of the peninsula rather than forcing a line through it, with ocean far below and mountains rising sharply inland.
The route continues towards Cape Point, where seabirds circle above the headlands and the scale of the coastline becomes clear.
We finish cycling in Simon’s Town at Boulders Beach, home to a protected colony of African penguins. We stop for lunch before taking a transfer to Stellenbosch in the heart of the Cape winelands. Depending on road closures, we either stay in Franschhoek or Stellenbosch.
Terrain: 100% paved.
Meals: Breakfast
Day 3
Through the Cape Winelands
Ride through the Cape Winelands today, where vineyards and mountain backdrops create a scenic cycling route.
We cycle through Franschhoek and Stellenbosch, two of the most iconic wine towns in South Africa, via vineyards and historic towns. Enjoy the peaceful countryside, with plenty of opportunities to slow down and take in the views. This route offers a mix of gentle climbs and scenic descents.
Terrain: 90% paved, 10% gravel
Meals: Breakfast
Day 4
Coastal ride to Pingle Bay, end in Botrivier
We transfer (45 minutes) to Gordons Bay Harbour. From here, we ride along the scenic coast past the quaint towns of Pringle Bay and Betty’s Bay to end in Botriver, while enjoying stunning sea views.
After lunch, we transfer to Houw Hoek Hotel, a historic hotel in apple country.
Terrain: 100% paved
Meals: Breakfast
Day 5
Cycle through vineyards and olive groves in the Robertson Valley
After a scenic one-hour transfer to the starting point, gear up for an exciting ride through the Robertson Valley, another renowned wine-producing region.
Our route includes tranquil roads surrounded by vineyards, olive groves, and expansive farmlands, offering a peaceful escape with views of the valley and mountains.
Terrain: 60% paved, 40% gravel
Meals: Breakfast
Day 6
Ride through the Breede River Valley to Montagu, then onto Barrydale
Set off for Montagu, part of the Little Karoo (or Klein Karoo) region. This ride, one of the most scenic routes in the Western Cape, takes you through the vast open landscapes of the Breede River Valley, with views of rugged mountains, expansive vineyards, and rural farmlands.
The terrain offers a mix of smooth stretches and gentle climbs, providing a perfect balance of challenges and relaxation. As you approach Montagu, known for its orchards, vineyards and hot springs, the landscape transitions into dramatic mountain passes, offering sweeping views that make every pedal stroke worthwhile.
We stop for lunch and have a chance to explore the quaint town before a transfer of around 30mins to Barrydale.
Terrain: 100% paved
Meals: Breakfast
Day 7
Cycle through the scenic Klein Karoo
We start this morning with a transfer along Route 62. We’ll stop at the famous Ronnie Sex Shop, an iconic roadside pub, before we embark on a captivating ride into the Klein Karoo. Keep your eyes peeled for animals roaming the rugged landscape, as we cycle through Van Wyksdorp before dropping into the Rooiberg Valley.
The route is lined with impressive mountain backdrops, with plenty of opportunities to stop and take in the views. Known for its rural beauty and tranquil atmosphere, this journey offers an immersive way to experience the heart of the Little Karoo.
Terrain: 15% paved, 85% gravel
Meals: Breakfast
Day 8
A day to rest, relax and take in the beauty of the Rooiberg
Enjoy a full day at leisure to relax and take in the beautiful surroundings of the Klein Karoo, where vast semi-desert plains are framed by rugged ridges and distant mountains. After several active days in the saddle, there’s time to unwind by the pool, enjoy the lodge spa, explore the walking trails or simply soak up the Karoo’s famously star-filled night skies.
Meals: Breakfast
Day 9
Cycle to Calitzdorp, testing yourself against the Rooiberg Pass
Start your day with a challenging yet rewarding ride to Calitzdorp, taking on the formidable Rooiberg Pass. As you ascend the pass, enjoy views of the rugged landscape and vast plains that stretch for miles, while also stopping for mid-morning snacks.
The descent into Calitzdorp offers a thrilling finish, with sweeping views of the Little Karoo’s unique terrain.
Wrap up the day with a transfer to Oudtshoorn, known for being the ostrich capital of the world.
Terrain: 35% paved, 65% gravel
Meals: Breakfast
Day 10
Explore natural wonders by bike
Today we take one of two routes, depending on whether the Swartberg Pass is open.
Option one, taken if the pass is open: Begin with a scenic transfer to the Cango Caves, a natural wonder in the Swartberg Mountains. Join an optional tour of the caves or grab a cup of coffee here. After a short transfer we arrive at Kobus se Gat, a famous farm stall where you can sample a traditional Karoo roosterbrood – fire-roasted bread served with sweet jam. We then gear up for a thrilling ascent of the Swartberg Pass. The climb offers challenging terrain, but the reward is panoramic views of the mountains and valleys. After reaching the summit, enjoy the exhilarating descent to the charming village of Prince Albert, a historic oasis where you can unwind, refuel, and soak in the character of this quaint Karoo town.
Terrain: 15% paved, 85% gravel
Distance covered: 20mi (32km)
Ascent: 2,510ft (765m); Descent: 3,353ft (1,022m); Activity hours: 4
Option two, taken in the event the pass is closed: From our hotel, we cycle through Lategansvlei in Oudtshoorn, where gravel roads wind between working farms, thornveld and distant koppies. Enjoy the open views with the Swartberg mountains gradually rising ahead. It is a peaceful, scenic stretch – dusty, open and beautifully remote – before joining the Matjiesrivier waterway. When we reach Kobus se Gat, a famous farm stall, make sure you sample a traditional Karoo roosterbrood – fire-roasted bread served with sweet jam. Finishing, we’re transferred back to Oudsthoorn.
Terrain: 33% paved, 67% gravel
Distance covered: 37mi (60km)
Ascent: 3,250ft (990m); Descent: 1,510ft (460m); Activity hours: 5
Meals: Breakfast
Day 11
Journey through the Karoo
The route we take today depends on which option was taken yesterday.
Option one: Start your ride in the peaceful village of Prince Albert and follow the quiet backroads that skirt the northern side of the Swartberg Mountains. The route winds through wide-open Karoo landscapes, passing farmland, koppies and rugged foothills with gentle rolling terrain. As you loop around the back of the range, the scenery gradually softens and opens toward the Klein Karoo basin.
Terrain: 100% paved
Distance covered: 45mi (73km)
Ascent: 3,274ft (998m); Descent: 3,205ft (977m); Activity hours: 5
Option two: From Oudtshoorn, the Vergelegen Road leads us east through open Klein Karoo farmland towards Dysselsdorp. The route is quieter and more rural than the main road, passing dry plains, scattered farms and broad views of the surrounding mountains. Along the way, you may spot livestock grazing in the fields, ostriches wandering near farm fences, and the occasional antelope or other Karoo wildlife. It is an easy, scenic stretch with a real backroad feel before reaching the small farming community of Dysselsdorp.
Terrain: 26% paved, 74% gravel
Distance covered: 20mi (32km)
Ascent: 1,150ft (350m); Descent: 3,205ft (310m); Activity hours: 3
Meals: Breakfast,Lunch,Dinner
Day 12
Explore the Kammanasie foothills
We leave De Rust on a short transfer and head east into the quiet backcountry roads leading toward the Kamanassie Mountains. The route rolls through farmland and wide-open valleys before narrowing into the more rugged, remote terrain of the Kamanassie foothills.
Expect winding gravel sections, rocky ridgelines, and a few river crossings as you make your way through this untouched mountain landscape.
Terrain: 100% gravel
Meals: Breakfast,Lunch,Dinner
Day 13
Journey from Karoo to coast
Begin your ride from the game lodge in the Outeniqua foothills. The route gradually climbs into cool, green stretches of indigenous forest, where the scenery shifts from open valleys to dense woodland and towering mountain views.
Winding along quiet backroads, head deeper into the Knysna forest, finishing at the iconic Big Tree − a majestic, centuries-old giant that marks a fitting end to this beautifully varied and scenic ride. We end with a transfer to our hotel, where we spend our final night together.
Terrain: 100% gravel
Meals: Breakfast,Lunch
Day 14
Adventure ends in Knysna
After an unforgettable cycling trip, we begin our return journeys home. If you’d like to extend your adventure, speak to your sales representative about extending your stay.
Meals: Breakfast
What’s included
What’s not included
Additional information
Food
Food on this trip is very similar to the kind of food you are used to at home, though there may be the opportunity to try local meats such as ostrich, kudu or eland. Vegetarians can be well catered for on this trip – please inform us before departure of any special dietary requests so our local team can be well prepared.
The provided water is safe, clean drinking water, normally from boreholes. It is not bottled water, however. If you would rather have bottled water then this will be at your expense, though we would encourage you to make use of the safe drinking water provided as this helps diminish plastic consumption.
Drinking water: While the tap water in South Africa is generally considered safe to drink, we recommend avoiding drinking directly from the taps during your stay. Standards and sensitivities can vary, and we want to make sure you stay well throughout your trip. For your comfort and peace of mind, we recommend using filtered or bottled water instead.
Rooiberg Pass Challenge to Calitzdorp
Conquer the gravel ramps and switchbacks of Rooiberg Pass before a flowing descent into Calitzdorp. This is classic Karoo riding—clean air, raw ridgelines and a tangible sense of achievement at every crest.
Carved through the ancient Cape Fold Belt, Rooiberg reveals layers of geology and hardy flora adapted to aridity. Calitzdorp, famed for fortified wines, greets riders with warm small-town hospitality under the watch of sun-baked hills.
Robertson Valley Vineyards & Olive Groves Ride
Cycle quiet farm roads in the Robertson Wine Valley, bordered by the serrated Langeberg Mountains. Vine rows, olive orchards and river-irrigated fields create a serene patchwork, with gravel stretches adding texture to a gentle day in the saddle.
Part of the famed Route 62 wine belt, Robertson blends fertile alluvial soils with cellar traditions renowned for chenin, shiraz and MCC. It’s a landscape of open horizons and working terroir—perfect for unhurried pedalling and vineyard-to-mountain photography.
Cape Winelands Ride: Stellenbosch & Franschhoek
Pedal through the Cape Winelands between Stellenbosch and Franschhoek, where vineyards stripe the valleys beneath granite peaks. Smooth tarmac and light gravel sections link oak-lined avenues, historic homesteads and farm roads scented with fynbos and fermenting cellars.
Founded by French Huguenots and Dutch settlers, these storied wine towns pair Cape Dutch gables with mountain drama from the Simonsberg and Drakenstein ranges. Rolling terrain and vineyard vistas make this a soul-soothing stage that spotlights South Africa’s long winemaking lineage.
Knysna Forest Ride to the Big Tree
Glide beneath the cool canopy of the Knysna Forest, following shaded lanes and ferny glades to the Big Tree, a venerable Outeniqua yellowwood towering above the forest floor. The air shifts from Karoo-dry to forest-damp as birdsong replaces open-country silence.
These indigenous Afromontane forests once harbored the fabled Knysna elephants and fueled a timber era that shaped the Garden Route. Finishing beneath a centuries-old giant brings the journey from interior to coast to a fitting, contemplative close.
Chapman’s Peak & Cape Point Coastal Ride with Boulders Penguins
Ride Chapman’s Peak Drive, a cliff-carved corniche where Atlantic swells boom below and sandstone crags tower above. Follow the peninsula’s curves toward Cape Point, skirting fynbos slopes in Table Mountain National Park before rolling into Simon’s Town and the granite boulders that shelter a colony of African penguins at Boulders Beach.
Engineered in the early 1900s, Chapman’s Peak rewards steady climbing with wide-angle sea views and ocean air. Coastal headlands host circling seabirds and seasonal whales, while the penguin colony offers intimate wildlife moments on protected boardwalks, underscoring South Africa’s conservation story.
Clarence Drive Coast: Gordon’s Bay to Betty’s Bay
Trace the shoreline along Clarence Drive (R44), a spectacular marine terrace that clings to folded mountains above False Bay. The route sweeps past secluded coves and kelp-fringed shallows, threading the floral treasure-house of the Kogelberg Biosphere Reserve.
Expect sea breeze, ocean panorama and rugged sandstone buttresses as you pass coastal hamlets like Pringle Bay and Betty’s Bay. In season, watch for distant whale blows; year-round, the Cape Floral Kingdom’s fynbos adds color and fragrance to this radiant coastal ride.
Breede River Valley to Montagu & Barrydale on Route 62
Ride across the Breede River Valley toward Montagu, where orchards, vineyards and stone outcrops meet the dramatic folds of the Cape ranges. Smooth surfaces and measured climbs usher in big-sky views and classic country scenery.
Montagu’s hot-springs heritage and Cape Dutch architecture reflect frontier-era prosperity on Route 62. The day culminates amid rugged hills and farmsteads near Barrydale, with the Cape Fold Belt’s geology framing a quintessential Western Cape tableau.
Klein Karoo Gravel: Van Wyksdorp to the Rooiberg Valley
Roll into the Little Karoo (Klein Karoo) on broad gravel, passing windmills, red soils and bossie scrub on the way to Van Wyksdorp and the Rooiberg Valley. The sense of space is palpable—quiet roads, high horizons and the soft crunch of tires on dust.
Route 62’s offbeat character colors the journey, from quirky farm stalls to far-flung hamlets. Keep watch for antelope on the margins as mountain backdrops shift with every turn, revealing the arid grace of South Africa’s interior.
Swartberg Pass Ascent & Prince Albert Descent
Climb the gravel masterpiece of Swartberg Pass, its dry-stone walls a testament to Victorian ingenuity by Thomas Bain. Crest among rust-red sandstone and roll down to Prince Albert, a handsome Karoo town framed by irrigated lanes and mountain light.
Built in the 1880s and protected as a national monument, the pass threads dramatic geology and sweeping panoramas. During your time in the Karoo, conditions may redirect this stage to a scenic Oudtshoorn backroads ride—equally atmospheric, with wide skies, farmsteads and riverbeds.
Karoo Backroads Ride: Prince Albert or Dysselsdorp
Spin along quiet Karoo backroads, where windpumps tick and koppies rise from tawny plains. Depending on conditions, the route may depart Prince Albert around the Swartberg’s northern skirts, or follow the Vergelegen Road east from Oudtshoorn toward Dysselsdorp.
Expect gentle rollers, far horizons and working farmland where ostriches and livestock punctuate the landscape. It’s a contemplative stage that showcases rural rhythms and the generous space that defines the Karoo.
Kammanassie Foothills Backcountry Gravel
Explore the rugged fringes of the Kammanassie Mountains on backcountry gravel, threading valleys and rocky ridgelines with occasional river crossings. The riding is immersive and tactile—dust, rock, water and the hush of seldom-travelled roads.
This biodiverse corridor between the Swartberg and Outeniqua ranges feels remote yet alive, with aloes, renosterveld and birdlife thriving in the folds. The sense of discovery builds as each watershed reveals a wilder, more elemental Cape landscape.
Cango Caves Guided Tour
Join a guided tour of the Cango Caves, a subterranean wonder beneath the Swartberg Mountains. Walk illuminated chambers where stalactites and stalagmites create organ pipes, flowstone draperies and echoing halls with names like Van Zyl’s Hall.
Formed over millions of years in dolomite and limestone, the caves reveal geological artistry and San Rock Art heritage in the wider region. This optional experience is at additional cost and bookable on tour, subject to availability and operating conditions.
Cape Town Welcome Dinner & Rider Briefing
Meet your tour leader and fellow cyclists in Cape Town for a convivial hosted welcome dinner that sets the rhythm of the journey. Share riding goals, swap first impressions and enjoy local flavors influenced by Cape Malay kitchens and Atlantic waters as the group bonds ahead of the miles to come.
Framed by Table Mountain, the city’s layered heritage provides a vibrant backdrop while your leader outlines highlights along Route 62, support arrangements, and safety essentials. It’s an engaging, practical start that equips you for South Africa’s varied terrain and spirited cycling culture.
