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.

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

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

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

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

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

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.

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

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

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

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

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

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.