Soil moisture measurement is essential to validate hydrological models and satellite data. In this work we provide an overview of different local and plot scale soil moisture measurement techniques applied in three different conditions in terms of altitude, land use, and soil type, namely a plain, a mountain meadow and a hilly vineyard. The main goal is to provide a synoptic view of techniques supported by practical case studies to show that in such different conditions it is possible to estimate a time and spatially resolved soil moisture by the same combination of instruments: contact-based methods (i.e., Time Domain Reflectometry-TDR, and two low frequency probes) for the time resolved, and hydro-geophysical minimally-invasive methods (i.e., Electromagnetic Induction-EMI, Ground Penetrating Radar-GPR, and the Electrical Resistivity Tomography-ERT) for the spatially resolved. Both long-term soil moisture measurements and spatially resolved measurement campaigns are discussed. Technical and operational measures are detailed to allow critical factors to be identified.