This work presents the results of an advanced geophysical characterization of a contaminated site, where a correct understanding of the dynamics in the unsaturated zone is fundamental to evaluate the effective management of the remediation strategies. Large-scale surface electrical resistivity tomography (ERT) was used to perform a preliminary assessment of the structure in a thick unsaturated zone and to detect the presence of a thin layer of clay supporting an overlying thin perched aquifer. Discontinuities in this clay layer have an enormous impact on the infiltration processes of both water and solutes, including contaminants. In the case here presented, the technical strategy is to interrupt the continuity of the clay layer upstream of the investigated site in order to prevent most of the subsurface water flow from reaching the contaminated area. Therefore, a deep trench was dug upstream of the site and, in order to evaluate the effectiveness of this approach in facilitating water infiltration into the underlying aquifer, a forced infiltration experiment was carried out and monitored using ERT and ground-penetrating radar (GPR) measurements in a cross-hole time-lapse configuration. The results of the forced infiltration experiment are presented here, with a particular emphasis on the contribution of hydro-geophysical methods to the general understanding of the subsurface water dynamics at this complex site.