The machining of free-formed surfaces, e.g., dies or moulds, is often affected by tool vibrations, which can affect the quality of the workpiece surface. Furthermore, in 5-axis milling, the dynamic properties of the system consisting of the tool, spindle and machine tool can vary depending on the tool pose. In this paper, a simulation-based methodology for optimising the tool orientation, i.e., tilt and lead angle of simultaneous 5-axis milling processes, is presented. For this purpose, a path finding algorithm was used to identify process configurations, that minimise tool vibrations based on pre-calculated simulation results, which were organised using graph theory. In addition, the acceleration behaviour of the feed drives, which limits the ability of adjusting the tool orientation with a high adaption frequency, as well as potential collisions of the tool, tool chuck and spindle with the workpiece were considered during the optimisation procedure.