This is the flagship. Depart Cape Town at 07:00 and drive north into the mountains while the roads are still empty. Bain’s Kloof is the first pass — one of the great roads in South Africa, built by convict labour in 1853, threading through sheer sandstone and raw fynbos. Du Toitskloof follows, sweeping down into the fertile valley beyond.
Coffee stop at 09:30 in Paarl — one of the Cape’s great historic wine towns — before the convoy continues south into Stellenbosch. Lunch at a wine estate under the oaks: seasonal food, local wine, a small tasting in line with local regulations. No rush.
The return is over Chapman’s Peak at golden hour. The road carved into the cliff, the Atlantic catching the last of the light. You arrive back in Cape Town as the sun touches the water.
The convoy assembles at our Cape Town base. A short walk-around of your 911 SC, radios synced with the guide vehicle, and you pull out onto empty morning roads heading north on the N1.
One of South Africa’s most dramatic mountain passes. The R303 winds through raw fynbos and sheer sandstone cliffs above the Witte River gorge. Built in 1853, it has never been widened. The 911 SC was made for exactly this kind of road.
A sweeping descent through the Huguenot Mountains into the valley beyond. Open hairpins, long sightlines, the Porsches in full stride. A viewpoint stop at the summit before dropping into the valley.
A relaxed stop in Paarl — one of the Cape’s oldest and most beautiful wine towns. Stretch, take in the mountain views, and let the morning’s driving settle before heading south toward Stellenbosch.
A long table under the oaks at one of Stellenbosch’s great estates. Seasonal food, local wine, a small tasting in line with local regulations. No rush — this is very much part of the experience. Water and gelato included.
The finale. The road carved into the cliff above the Atlantic, the sky turning gold, the ocean a hundred metres below. You arrive back in Cape Town as the sun touches the water.
Your choice of Silver, White or Guards Red coupé. Fully insured, fully fuelled, immaculately presented.
Your guide leads from the front vehicle with 2-way radio communication throughout. Local knowledge, perfect pacing, and an instinct for the right stop.
A full lunch at a premium Stellenbosch estate. Food, drinks, a small wine tasting, water and gelato. No supplements, no surprises.
Comprehensive cover for every car on every road. Drive with complete confidence.
A mid-morning break in Paarl before lunch.
A printed route card and map for every guest. A keepsake from the day.
R 8,000 per person · All-inclusive · Maximum 6 guests
Make an Enquiry View all toursThe Winelands Day Tour runs on request — we keep the convoy to a maximum of six guests so the day stays personal. Send your details and we’ll confirm availability within 24 hours.