Italy was the first European country to be significantly impacted by the COVID-19 pandemic. The lack of similar previous experiences and the initial uncertainty regarding the new virus resulted in an unpredictable health crisis with 243,506 total confirmed cases and 34,997 deaths between February and July 2020. Despite the panorama of precariousness and the impelling calamity, the country successfully managed many aspects of the early stages of the health and socio-economic crisis. Nevertheless, many disparities can be identified at the regional level. The study aims to determine which aspects of regional management were considered more important by the citizens regarding economic and health criteria. A survey was designed to gather responses from the population on the Italian regions’ response and provide a ranking of the regions. The 29-item online survey was provided to 352 individuals, and the collected data were analyzed using the Analytic Hierarchy Process methodology. The results show a general agreement in considering of greater relevance the healthcare policies rather than the economic countermeasures adopted by regional governments. Our analysis associated a weight of 64% to the healthcare criteria compared to the economic criteria with a weight of 36%. In addition to the results obtained from the Analytic Hierarchy Process, the sample’s composition was analyzed to provide an overall assessment of the Italian regions. To do so, we collected objective data for each region and multiplied them by the overall weight obtained for each sub-criteria. Looking at the propensity to vaccination or the belief in a relation between COVID-19 and 5G according to age and educational qualification helps understand how public opinion is structured according to cultural and anthropological differences.