Artificial Intelligence, Big Data, blockchain, automation, IoT, and 5G represent fundamental knowledge for the evolution of the modern society. The smart label initially found breeding ground in urban settings giving rise to Smart Cities which are capable of efficiently supplying resources and services through the use of technology. The “new” incentives coming from Information Communication Technology (ICT) have over time positively involved other spatial realities as well: Smart Villages, Smart Tourism Destinations, and Smart Ports. The latter spatial context is proposed in all its complexity as it includes various stakeholders, internal and external, and requires constant operational commitment. In order to meet the sustainability goals dictated by international documents (Agenda 2030 and 2050), the operational chain of the port system must adopt an innovative approach capable of improving and optimizing the competitiveness and the active and functional activities of the operators involved. After a brief literature review of the concept of smartness around the port world, this paper aims to highlight the fundamental role played by Spanish Port Authorities to propose training projects that can also educate and make human capital “smart”.