Assessment of soil water repellency (SWR) was conducted in the decomposed organic floor layer (duff) and in the mineral soil layer of two Mediterranean pine forests, one in Italy and the other in Spain, by the widely-used water drop penetration time (WDPT) test and alternative indices derived from infiltration experiments carried out by the minidisk infiltrometer (MDI). In particular, the repellency index (RI) was calculated as the adjusted ratio between ethanol and water soil sorptivities whereas the water repellency cessation time (WRCT) and the specifically proposed modified repellency index (RIm) were derived from the hydrophobic and wettable stages of a single water infiltration experiment. Time evolution of SWR and vegetation cover influence was also investigated at the Italian site. All indices unanimously detected severe SWR conditions in the duff of the pine forests. The mineral subsoils in the two forests showed different wettability and the clay-loam subsoil at Ciavolo forest was hydrophobic even if characterized by organic matter (OM) content similar to the wettable soil of an adjacent glade. It was therefore assumed that the composition rather than the total amount of OM influenced SWR. The hydraulic conductivity of the duff differed by a factor of 3.8–5.8 between the two forested sites thus influencing the vertical extent of SWR. Indeed, the mineral subsoil of Javea showed wettable or weak hydrophobic conditions probably because leaching of hydrophobic compounds was slowed or prevented at all. Estimations of SWR according to the different indices were in general agreement even if some discrepancies were observed. In particular, at low hydrophobicity levels the SWR indices gathered from the MDI tests were able to signal sub-critical SWR conditions that were not detected by the traditional WDPT index. The WRCT and modified repellency index RIm yielded SWR estimates in reasonable agreement with those obtained with the more cumbersome RI test and, therefore, can be proposed as alternative procedures for SWR assessment.