Soil erosion is one of the most widespread soil degradation phenomena worldwide. Mediterranean landscapes, due to some peculiar characteristics, such as fragility of soils, steep slopes, and rainfall distribution during the year, are particularly subject to this phenomenon, with severe and complex issues for agricultural production and biodiversity protection. In this paper, we present a diachronic approach to the analysis of soil loss, which aims to account for climate variability and land cover dynamics by using remote data about rainfall and land cover to guarantee sufficient observational continuity. The study area (Basilicata, Southern Italy) is characterized by different local climates and ecosystems (temperate, Csa and Csb; arid steppic, Bsk; and cold, Dsb and Dsc), and is particularly suited to represent the biogeographical complexity of the Mediterranean Italy. The well-known Revised Universal Soil Loss Equation (RUSLE) was applied by integrating information from remote sensing to carry out decadal assessments (1994, 2004, 2014, and 2021) of the annual soil loss. Changes in the rainfall regime and vegetation cover activity were derived from CHIRPS and Landsat data, respectively, to obtain updated information useful for dynamical studies. For the analyzed region, soil loss shows a slight reduction (albeit always remarkable) over the whole period, and distinct spatial patterns between lowland Bsk and Mediterranean mountain Dsb and Dsc climate areas. The most alarming fact is that most of the study area showed soil erosion rates in 2021 greater than 11 t/ha*y, which is considered by the OECD (Organization for Economic Cooperation and Development) the threshold for identifying severe erosion phenomena. A final comparison with local studies shows, on average, differences of about 5 t ha−1 y−1 (minimum 2.5 and maximum 7) with respect to the local estimates obtained with the RUSLE model. The assessment at a regional scale provided an average 9.5% of soil loss difference for the arable lands and about 10% for all cultivated areas. The spatial-temporal patterns enhance the relevance of using the cover management factor C derived from satellite data rather than land cover maps, as remote observations are able to highlight the heterogeneity in vegetation density within the same vegetation cover class, which is particularly relevant for agricultural areas. For mountain areas, the adoption of a satellite-gridded rainfall dataset allowed the detection of erosion rate fluctuations due to rainfall variability, also in the case of sparse or absent ground pluviometric stations. The use of remote data represents a precious added value to obtain a dynamic picture of the spatial-temporal variability of soil loss and new insights into the sustainability of soil use in a region whose economy is mostly based on agriculture and the exploitation of natural resources.