South Side Cycles creates premium cycling holidays for people who like to travel well and ride properly. Born in Cape Town and shaped by a love of road, gravel and mountain biking, we design considered small-group and private journeys in South Africa and selected destinations worldwide.

We believe the best trips have a strong sense of place. They follow roads with a reason to ride them, gravel that takes you beyond the usual route, and trails that leave you feeling like you have seen a side of a destination few visitors reach. The riding matters, but so does everything around it: where you stay, how the day flows, the people you meet and the ease of knowing the details have been taken care of.

Every South Side Cycles holiday is planned with care, from route selection and bike-friendly accommodation to practical ride support, luggage logistics and local experiences. We work with trusted guides, hotels and partners who understand what cyclists need after a full day outside.

Our trips are for riders who value good terrain, comfortable stays, thoughtful service and the company of people who enjoy the same things. Whether you join a scheduled departure or bring your own group, we make it easier to spend your time doing what you came for: riding somewhere worth riding.