Simulation-based analysis of fitness landscapes with application to the vehicle scheduling problem with time windows is discussed in the paper. Methods of analysis of fitness landscapes and measures known in literature are reviewed. The procedure for simulation based analysis of fitness landscape is introduced. The tool that allows automating this analysis is described. The simulation model is developed within AnyLogic 6 simulation software, while Java applications generate landscape path solutions, analyse their fitness values series and implement a genetic algorithms. Experimental study for a vehicle scheduling problem with the time windows is given and demonstrates the main steps of fitness landscape applied to optimization problem.