Truck drayage operations are essential to link logistics nodes in the port and beyond. Truck drayage services mainly involve the short-distance transportation of cargo from/to facilities in the proximity of ports as well as inter-terminal transports . Often, those transports are planned by a third-party drayage operator (e.g., an intermodal transport provider) and assigned to self-employed truck operators, referred to as truckers. In the Port of Hamburg, for example, about 90% of inter-terminal transports are handled by truck and severely contribute to the road traffic volumes and situation at gates. Besides this, many ports increasingly suffer from peak transport demands due to the ever-increasing size of container vessels.