Global transportation knows many different modalities – goods arrive from far away places by ship, plane, railway, or truck. Airports and seaports both represent important nodes within the global transportation network. Both show distinct characteristics, but also similarities when it comes to challenges like required flexibility, robustness, reliability and situational awareness of the stakeholders involved. In this article, we introduce two different simulation games addressing some of these challenges in two complex transportation nodes and discuss the qualitative results of user tests with the games. Within a comparative section, we show how simulation games can be used to address the challenges of multimodal transportation.