Relying on the international 2030 Agenda and specifically applying sustainable development’s triple bottom line to port operations, innovation technologies enabled by 5G transformation have shown to serve as a junction point between the UN Sustainable Development Goals (SDGs) and the port’s Key Performance Indicators (KPIs). In order to measure economic, social and financial benefits deriving from 5G networks and digital transformation, a piloted technology model has been shaped with the final aim of designing new models of port management and operational planning, and of implementing sustainable port growth policies. Such an assessment finally represents a crucial means to enhance technological advancements on port competitiveness and efficiency, and to boost sustainability performance by supporting public policies and business decisions, finally leading to the development of the port of the future.