Ports are crucial links in supply chains, creating wealth for adjacent regions. Concerning port competitiveness, it is indicated in literature that good hinterland connections are crucial. Therefore, this chapter offers a framework to make decisions about hinterland connections. To do this, analysis of scientific studies and consulting reports was conducted in combination with discussions with experts. Last, the structure of analysis is applied upon the Port of Zeebruges, which features a strong imbalance between its strong maritime potential, and the relatively weak hinterland connections. The analysis results in strategies of optimizing the strategic decision making. From the real option theory, it is clear that a phased strategy is most suitable. The integrated analysis provides a framework to make investment decisions about port investments in general and hinterland connections in particular, and a pathway solution to a concrete case. Therefore, the study is relevant for policy makers and scientific researchers.