The fourth industrial revolution, known as “Marine 4.0”, has brought the digital era into marine operations. The availability of large amounts of data from ships combined with the use of digital technologies has enabled new and better functions in the area of operation and safety of the ships. The results of several research projects around the world have shown that autonomous ship operation is an objective that can be achieved but there are open-ended issues that need to be addressed. Regulations are part of them. In the last April session of the Maritime Safety Committee, IMO approved a road map containing a work plan for the development of a non-mandatory Code, with a view to adoption in 2024 as the first stage. Based on the experience from the application of the non-mandatory Code, a mandatory Maritime Autonomous Surface Ship (MASS) Code will be developed which is envisaged to enter into force on 1 January 2028. Regulations are essential to ensure a reliable and safe operation nevertheless, the human factor plays an important role. As with any new technology, there must be a paradigm shift in seafarers’ education and training models, including the requirement for new and additional skills. The situation becomes more critical at the level of cadet officers, where we have a lack of experience at sea and a very basic educational level of nautical schools in the fields of study of automation and other new digital technologies. The Italian Maritime Academy has studied this question and has a new educational model, which is based on an analysis of current and future skills requirements. The first outcome of this analysis is the need to change the educational approach from “teaching to know” to “learning to learn”, meaning the ability to organize one’s own learning through effective time and information management. The educational model is based on a triangle of skills including sustainability, hard skills, and soft skills. Sustainability is the study of the impact of the vessels on the environment, the decarbonization process, regulations for pollution prevention, new fuels, and energy-saving systems. Hard skills studies are focused on electrical and hybrid systems, the new digital technologies such as Big Data, the Internet of Things, Augmented Reality, and Artificial Intelligence, and their area of applications in the marine industry. Cybersecurity and risk management are included in the program study. The soft skills that have been identified as necessary for the cadet officers are problem-solving, teamwork, conflicts management, effective communication, leadership, and situational awareness. The final goal is to have cadets that can operate as officers on board any vessel, according to the four degrees of autonomy defined by the IMO MASS provisions. The use of simulators, cooperation with industry, self-assessment and continuous learning, “train the trainer”, and job rotation schemes from ship to shore, are other milestones of an integrated approach to the education of the next generation seafarers.