Fluctuations in climatic conditions during the growing season are recorded in Mediterranean tree-rings and often result in intra-annual density fluctuations (IADFs). Dendroecology and quantitative wood anatomy analyses were used to characterize the relations between the variability of IADF traits and climatic drivers in Pinus pinaster Aiton and Quercus ilex L. growing at sites with different water availability on the Elba island in Central Italy. Our results showed that both species present high xylem plasticity resulting in the formation of L-type IADFs (L-IADFs), consisting of earlywood-like cells in latewood. The occurrence of such IADFs was linked to rain events following periods of summer drought. The formation of L-IADFs in both species increased the hydraulic conductivity late in the growing season, due to their larger lumen area in comparison to "true latewood". The two species expressed greater similarity under arid conditions, as unfavorable climates constrained trait variation. Wood density, measured as the percentage of cell walls over total xylem area, IADF frequency, as well as conduit lumen area and vessel frequency, specifically in the hardwood species, proved to be efficient proxies to encode climate signals recorded in the xylem. The response of these anatomical traits to climatic variations was found to be species- and site-specific.