The increase in atmospheric and soil temperatures in recent decades has led to unfavorable conditions for plants in many Mediterranean coastal environments. A typical example can be found along the coast of the Campania region in Italy, within the “Volturno Licola Falciano Natural Reserve”, where a pine forest suffered a dramatic loss of trees in 2021. New pines were planted in 2023 to replace the dead ones, with a larger tree layout and interspersed with Mediterranean bushes to replace the dead pine forest. A direct (in situ) monitoring program was planned to analyze the determinants of the pine salinity stress, coupled with Sentinel-2 L2A data; in particular, multispectral indices NDVI and NDMI were provided by the EU Copernicus service for plant status and water stress level information. Both the vadose zone and shallow groundwater were monitored with continuous logging probes. Vadose zone monitoring indicated that salinity peaked at a 30 cm soil depth, with values up to 1.9 g/L. These harsh conditions, combined with air temperatures reaching peaks of more than 40 °C, created severe difficulties for pine growth. The results of the shallow groundwater monitoring showed that the groundwater salinity was low (0.35–0.4 g/L) near the shoreline since the dune environment allowed rapid rainwater infiltration, preventing seawater intrusion. Meanwhile, salinity increased inland, reaching a peak at the end of the summer, with values up to 2.8 g/L. In November 2023, salts from storm-borne aerosols (“sea spray”) deposited on the soil caused the sea-facing portion of the newly planted pines to dry out. Differently, the pioneer vegetation of the Mediterranean dunes, directly facing the sea, was not affected by the massive deposition of sea spray. The NDMI and NDVI data were useful in distinguishing the old pine trees suffering from increasing stress and final death but were not accurate in detecting the stress conditions of newly planted, still rather short pine trees because their spectral reflectance largely interfered with the adjacent shrub growth. The proposed coupling of direct and remote sensing monitoring was successful and could be applied to detect the main drivers of plant stress in many other Mediterranean coastal environments.