In the last few decades, many institutional initiatives have remarked that gross domestic product is unable to capture all aspects of well-being within society. At the same time, in some countries, such as Italy, this theme is still under study because recent research has pointed out this country is arguably the only Western nation where regional imbalances still play a meaningful role nowadays. The present research aims to examine the overall satisfaction of Italians, at a local level, and the perception they have about the country’s priority problems. The analysis tends to discern the evolution of the above aspects in four distinct stages, i.e. 2000–2005–2010–2015. Precisely, the objective is to understand if and how the sense of satisfaction and perception of some aspects of everyday life has evolved. Using the data collected by ISTAT within the multi-purpose project survey “Daily life aspects”, twenty-six subjective social indicators, which express the level of satisfaction of some aspects of one’s life and the judgment on problems of one’s context, are contemplated. The k-means cluster analysis is applied to identify homogeneous groups of regions based on the chosen indicators and the evolution of their composition and characteristics over time. Our findings show that there are significant and exciting regional characterisations. Notably, people living in southern Italy suffer most from unemployment and poverty whereas the regions with the most populated cities are dissatisfied with traffic and pollution. Policymakers must, therefore, consider these people’s priority problems to evaluate the impacts that the political actions may have at an economic, social and territorial level.