Although the Port of Tallinn is located on the Baltic Sea and the Port of Koper on the Adriatic Sea, these two ports have similar cargo volumes and receive a similar number of cargo ships each year, while the difference is in container and passenger volume. In addition to a comparative analysis of the performances of these two ports, we analyze the level of their preparedness to meet the challenges of cyber threats. In this direction, extensive research was carried out in relevant secondary sources, while in-depth interviews and surveys were conducted with the important cybersecurity officers in the ports of Tallinn and Koper. The aim is to draw attention to the importance of coordinating ports’ defences against cyber risks across different geo-political regions and dynamics.