The invention relates to a planning system and method for operating one or more road milling machines. In that context, material properties of a road are captured and are geographically associated with one or more roads or road segments. Based on the material properties, an expected milling output of a road milling machine is ascertained, in the context of carrying out milling tasks on the road, or an expected wear on the milling tools. An optimized sequence of milling tasks to be carried out is created on the basis of those data. Accordingly, the invention may enable optimized deployment of the one or more road milling machines and of resources necessary for carrying out the road milling tasks. Aspects of the planning system may be remotely implemented for centralized application with respect to each of the road milling machines, or locally implemented for individual road milling machines.