Surface soil moisture is a key hydrologic state variable that greatly influences the global environment and human society. Its significant decrease in the Mediterranean region, registered since the 1950s, and expected to continue in the next century, threatens soil health and crops. Microwave remote sensing techniques are becoming a key tool for the implementation of climate-smart agriculture, as a means for surface soil moisture retrieval that exploits the correlation between liquid water and the dielectric properties of soil. In this study, a workflow in Google Earth Engine was developed to estimate surface soil moisture in the agricultural fields of the Marche region (Italy) through Synthetic Aperture Radar data. Firstly, agricultural areas were extracted with both Sentinel-2 optical and Sentinel-1 radar satellites, investigating the use of Dual-Polarimetric Entropy-Alpha decomposition's bands to improve the accuracy of radar data classification. The results show that Entropy and Alpha bands improve the kappa index obtained from the radar data only by 4% (K = 0.818), exceeding optical accuracy in urban and water areas. However, they still did not allow to reach the overall optical accuracy (K = 0.927). The best classification results are reached with the total dataset (K = 0.949). Subsequently, Water Cloud and Tu Wien models were implemented on the crop areas using calibration parameters derived from literature, to test if an acceptable accuracy is reached without in situ observation. While the first model’s accuracy was inadequate (RMSD = 12.3), the extraction of surface soil moisture using Tu Wien change detection method was found to have acceptable accuracy (RMSD = 9.4).