Being located in the middle of Southern Europe, and thus likely representing a particularly dynamic member of Mediterranean Europe, Italy has experienced a sudden increase in early desertification risk because of multiple factors of change. Long-term research initiatives have provided relatively well-known examples of the continuous assessment of the desertification risk carried out via multiple exercises from different academic and practitioner stakeholders, frequently using the Environmentally Sensitive Area Index (ESAI). This composite index based on a large number of elementary variables and individual indicators—spanning from the climate to soil quality and from vegetation cover to land-use intensity—facilitated the comprehensive, long-term monitoring of the early desertification risk at disaggregated spatial scales, being of some relevance for policy implementation. The present study summarizes the main evidence of environmental monitoring in Italy by analyzing a relatively long time series of ESAI scores using administrative boundaries for a better representation of the biophysical and socioeconomic trends of interest for early desertification monitoring. The descriptive analysis of the ESAI scores offers a refined representation of economic spaces in the country during past (1960–2010 on a decadal basis), present (2020), and future (2030, exploring four different scenarios, S1–S4) times. Taken as a proxy of the early desertification risk in advanced economies, the ESAI scores increased over time as a result of worse climate regimes (namely, drier and warmer conditions), landscape change, and rising human pressure that exacerbated related processes, such as soil erosion, salinization, compaction, sealing, water scarcity, wildfires, and overgrazing.