AI, Big Data, the Internet of Things, and chains are new radical technologies that shape a new economy and society. In 2022, according to the Digital Economy and Society Index, the digital gap is at the European level around 46% of individuals lack basic digital skills, which in Romania is 72% and in Italy 54%. That means that according to the European Commission’s Skills Agenda and the Digital Education Action Plan for 2025, around 70% of adults have basic digital skills; according to Digital Compass, by 2030, at least 80% of individuals and to reduce the digital gap for the gymnasium graduates from 30% in 2019 to 15% in 2030. Education systems must facilitate processes to adapt human capital to this new reality. The question is: “Where and when should digital skills be tested and certified to effectively bridge the digital gap at the NUTS2 level in Italy and Romania?” The research methodology is Multivariate Clustering analysis at NUTS 2 level in Arc GIS Pro 3.2. Data used from Digital Barometer 2023 QB2.4. Mapping clusters by classes of similar observations are relevant for digital gap-filling. The main implication of this research is that the educational system increases its ability to provide workers and future workers with the lifelong skills demanded by a highly dynamic, changing economic world driven by technological progress. Our main contribution to the field of studies is to better understand the digital divide at the regional level with a focus on basic digital skills acquired in mass.