The Mediterranean region is an area particularly susceptible to water scarcity and drought. In this work, drought has been analyzed in Italy using multiple timescales of the standardized precipitation index (SPI) evaluated from the Integrated Multi-satellitE Retrievals for Global Precipitation Measurement product from 2000 to 2020. In particular, drought characteristics (severity, duration, and intensity) have been estimated by means of the run theory applied to the SPI values calculated in 3325 grid points falling within the Italian territory. Results clearly indicate that although a high number of drought events has been identified for the short timescale, these events present a lower duration and lesser severity than the long-timescale droughts. The main outcomes of this study, with the indication of the spatial distribution of the drought characteristics in Italy, allow identifying the areas that could also face water stress conditions in the future, thus requiring drought monitoring and adequate adaptation strategies.