One of the crucial challenges of maritime transport is digitalization through the implementation of proper IT solutions. Development and deployment of such solutions allows seaports to increase their overall efficiency, to lower costs and improve performance times of the intra-terminal operations, to improve information flow and decision-making and to decrease the environmental footprint by addressing the sustainability. Nevertheless, the digitalization levels are heterogeneous and depend on different factors, such as seaport size, cargo volumes and type, stakeholders’ needs, business models and investments. We propose a prototyping framework for agile smart service development relying on a set of standard and open-source technologies. The proposed framework is validated at The Port Network Authority of the Northern Tyrrhenian Sea (Port of Livorno) and the transferability of research results is assessed against the Port of Singapore, the most important hub of the Asian region.