Validation of soil moisture products derived from synthetic aperture radar (SAR) remotely sensed observations involves a comparison against ground-truth data. This validation step helps one to state the performance of competing retrieval algorithms. Nevertheless, the design of a field experiment in the context of SAR retrieval is not straightforward. Ground-based measurements are affected by instrument errors due to both the physical limitations of the measurement technique and the uncertainties related to the spatial variability of the soil moisture. To properly assess the performance of the retrieved estimates, both of the mentioned sources of uncertainties should be considered in the ground-based sampling and in the subsequent error assessment analysis. This letter addresses the rationale behind an optimal field experiment designed to assess the suitability of soil moisture retrieval algorithms.