This study aims to examine interactions between tree characteristics, sap flow, and environmental variables in an open Pinus brutia (Ten.) forest with shallow soil. We examined radial and azimuthal variations of sap flux density (Jp), and also investigated the occurrence of hydraulic redistribution mechanisms, quantified nocturnal tree transpiration, and analyzed the total water use of P. brutia trees during a three-year period. Sap flow and soil moisture sensors were installed onto and around eight trees, situated in the foothills of the Troodos Mountains, Cyprus. Radial observations showed a linear decrease of sap flux densities with increasing sapwood depth. Azimuthal differences were found to be statistically insignificant. Reverse sap flow was observed during low vapor pressure deficit (VPD) and negative air temperatures. Nocturnal sap flow was about 18% of the total sap flow. Rainfall was 507 mm in 2015, 359 mm in 2016, and 220 mm in 2017. Transpiration was 53%, 30%, and 75%, respectively, of the rainfall in those years, and was affected by the distribution of the rainfall. The trees showed an immediate response to rainfall events, but also exploited the fractured bedrock. The transpiration and soil moisture levels over the three hydrologically contrasting years showed that P. brutia is well-adapted to semi-arid Mediterranean conditions.