Italian stone pine is a landmark of Mediterranean coastal areas. Today, pinewoods represent environmental amenity areas at risk, being under siege from intensive urbanisation. We present an emblematic case study in Rome’s coastal strip where urban encroachment around pinewoods is somewhat overlooked by urban planning, which may be threatening for their conservation. We studied: (i) changes in land use intensification in the pinewoods’ surroundings over the past 60 years (1949–2008), by means of a synthetic index of landscape conservation (ILC) ranging from 0 (maximum level of anthropogenic landscape alteration) to 1 (maximum level of landscape naturalness); (ii) influence of different landscape protection level on land use intensification. Findings show that in areas with low levels of landscape protection, the ILC had been decreasing in the first 100-m surrounding pinewoods, and within the 1-km buffer. The ILC had been rather stable within areas with high levels of landscape protection. Lessons learnt have implications for spatial development strategies to protect coastal pinewoods from external pressures due to future (planned) urban densification in their surroundings.