Days start early and are built around the ride. On day one, check-in is from 14:00, then the bikes get set up and the group rolls out for a short introduction ride around Stellenbosch so the fit can be fine-tuned and the guides can see how everyone rides. From there the week moves between the Winelands and the coast, with transport to the further start points included.

The Cape Town day is the one people talk about: a drive from Stellenbosch into the city, then a ride along the Atlantic through Camps Bay and Hout Bay and over Chapman's Peak Drive. You're welcome to stay in Cape Town afterwards to explore while the bikes go back to Stellenbosch. The Winelands day starts from the door, through vineyards and mountain valleys on quiet country roads. The Franschhoek day goes over Helshoogte and back the same way, with Franschhoek Pass as an optional extra climb depending on fitness and weather. Clarence Drive is a drive to the False Bay coast first, then sweeping ocean views with mountains rising straight out of the sea through Gordon's Bay, Rooi-Els and towards Betty's Bay. Bainskloof is the long mountain day — quiet roads, a historic pass and long climbs with sweeping descents around Wellington. The final ride is chosen on the day: a favourite area again, another local route, or a relaxed roll through the Winelands.

What separates this from a generic cycling holiday is the flexibility. Nothing is fixed to a schedule — the itinerary shifts with wind, weather and road conditions, which is how the guides pick the best ride for each day rather than forcing a plan that doesn't suit the conditions. Riders on the trip have included triathletes training for Ironman, and the guiding comes from Annchen Clarke, a Kona World Championships finisher, and Bram Peereboom, an MTB champion — both named in rider reviews on the page.

Stellenbosch itself is the base, in the heart of the Cape Winelands. Restaurants, cafés, shops and wine bars are within easy reach of central accommodation, and many rides start directly from town. For larger groups, clubs and teams, accommodation is usually arranged at the Stellenbosch Academy of Sport, a facility built for visiting athletes and teams, which works well when a group needs to stay together with bikes and transport in one place.

Off the bike, one afternoon goes to Villiera Wines for a tasting and a game drive through their wildlife sanctuary. One sports massage is included and scheduled around the riding; more can be arranged on request.

What's included

- 6 fully guided road rides - Short introduction and bike setup ride - Premium carbon road bike (Trek fleet, set up to your measurements) - Cape Town airport transfers - Transport to selected ride start points - Villiera wine tasting and game drive - One sports massage in Stellenbosch - Routes tailored to your fitness and experience - Mechanical support and bike setup throughout the week - 7 nights' accommodation (accommodation packages only)

What's not included

- Flights - Meals - Personal expenses - Di2 electronic shifting bike upgrade (R2,000 for the week) - Additional sports massages beyond the one included - Accommodation on the riding-only packages (1 Cyclist and 2 Cyclists)