Land use by humans strongly alters the landscape mosaic, either by reducing or increasing its heterogeneity. One of the most recent and widespread land use changes in Europe has been the spontaneous reforestation of marginal agricultural lands. These primarily affected small landscape patches, such as trees outside forests (TOF) and small open areas (SOA), often represent the most diversifying features of landscape’ structures. Nevertheless, only small-scale studies can be found in the literature and thus it remains a relatively unexplored issue. Integrating inventory and cartographic approaches, this work assesses changes in abundance, coverage, and average size of small patches in Italy between 1990 and 2013. Main results showed an overall increase in number and coverage of small patches during the reference period. The average patch size remains unaltered for TOF but decreases significantly for SOA, due to trees encroachment and canopy cover increasing in forests. Our findings confirm the important changes in Mediterranean land mosaics and contribute to a better understanding of current conditions and recent trends regarding TOF and SOA. The integrated approach has proven to be helpful for the large-scale assessment of small patches dynamics, representing a viable monitoring tool to encourage the inclusion of small patches in landscape policy and planning.