Mountain cultural landscapes of southern Europe have been affected during the 20th century by significant land use changes, due to depopulation and abandonment of traditional agro-silvo-pastoral practices. In addition, the cessation of traditional forest management led to a homogenization of forest structures and to the loss of habitats. Italy is one of the European countries most affected by the consequences of depopulation of mountain areas. Moscheta is located in the Italian Apennines, in Tuscany, and its economy has been based for centuries on forests (for timber, firewood, charcoal, and chestnuts to produce flour) and livestock. The aim of the paper is to analyze the land use changes occurred in a typical forest mountain landscape of southern Europe in the last 191 years, and to describe the characteristics and the results of the Forest Landscape Restoration project recently implemented. The methodology is based on GIS-based spatial analyses comparing the landscape of 1832, 2013 and 2023. In the period 1832–2013, 45% of the total surface was affected by forestation (average rate of 1.9 ha/year) mainly due to the abandonment of pastures and wooded pastures, but also to direct conifer afforestation. Chestnut groves were abandoned as they were no more economically interesting. From the 2010s, a Forest Landscape Restoration (FLR) project was implemented considering the economical, technical and future management feasibility. It focused on recovering the monumental chestnut groves and the wooded pastures, but also on interventions to increase the touristic attractiveness (paths management, Historical Landscape Museum creation, traditional buildings for chestnut drying restoration). The area was also inscribed in 2016 in the National list of Historical Rural Landscape established by the Italian Ministry of Agriculture. The analyses of the 2013–2023 landscape changes demonstrated that 4 ha of historical chestnut groves and 6.5 ha of wooded pastures have been recently restored, bringing their total surface to 17 ha and to 67 ha, respectively. In addition, results demonstrate that forestation completely stopped in the last 10 years. Other interventions are planned for the future: maintenance of chestnut groves, rehabilitation of other wooded pastures, re-introduction of the traditional practice of pollarding on ten beech trees. This study represents the first assessment of the FLR carried out in Moscheta, and demonstrates that the restoration of open spaces and of cultural forests is possible and could have a big impact on mountain cultural landscapes, contributing to the preservation and enhancement of ecosystem services and of touristic attractiveness, with potential direct benefits on the local economy.