This paper deals with designing and developing a Decision Support System (DSS) that will be able to manage the flow of goods and the business transactions between a port and a dry port. An integrated DSS architecture is proposed and specified and the main components are designed on the basis of simulation and optimization modules. In order to show the use and implementation of the DSS, this work tests and analyzes the case of the area of the Trieste port and manages the export flows of freights between a dry port and a seaport. An integrated approach is designed mainly at tactical and operational decision level exploiting simulation and optimization approaches and especially metaheuristic approaches