As the margins for improvements in the current freight transport system become limited, researchers address more and more the importance of collaboration between the actors which is crucial for the implementation of new, more efficient transport concepts as synchromodality. In addition, rail is concerned as a sustainable mode of transport that can also achieve economies of scale due to its ability to haul large quantities of goods. This study investigates cooperation policies that affect actors’ behavior to better utilize the rail use and lead to a more efficient system. We propose an innovative approach that combines gaming, simulation and optimization as a mixed method to test and evaluate these policies. The port to hinterland freight transportation system in the range of Port of Rotterdam is used as a case study. First, gaming sessions are organized in order to observe actors’ behavior and collect data. The game that is used was initiated by Port of Rotterdam, especially to identify the problems in this system. Subsequently, by assessing the observed data, a simulation model is developed and different policy scenarios are simulated to quantify their performance. In addition, the optimization model is developed, which sets the upper bound for performance and used as a solid base for comparison between the policy alternatives. Finally, the explanation of the difference between the policies’ and the optimized performance can give an insight on what are the root causes of the inefficiency, what is the best allocation of the resources and where the solutions should be focused.