The definition of the shear wave velocity profile is a fundamental step for the seismic characterization of a site in the context of Eurocode 8 and for the conduction of earthquake geotechnical engineering efforts such as site response analysis. Shear wave velocity profiles can be obtained: (1) directly from seismic geophysical and seismic geotechnical tests; or (2) indirectly, from “static” in-situ geotechnical tests such as dilatometer tests (DMT) and cone penetration tests (CPT). In the latter approach, shear wave velocity is estimated by using transformation models which are typically derived from data collected at other sites. This paper illustrates the procedures and main results of the comparative assessment of the performance of existing DMT-based and CPT-based transformation models to estimate shear wave velocity at two adjacent spatial locations in a rural site in the region of Tuscany in central Italy. Model-predicted shear wave velocity profiles were compared with direct measurements obtained by geophysical seismic dilatometer (SDMT) testing. The comparative assessment involved the definition, calculation, and assessment of quantitative performance statistics. The paper provides a critical analysis and a discussion of the outcomes with respect to soil type.