In bare soils of semi-arid areas, surface crusting is a rather common phenomenon due to the impact of raindrops. Water infiltration measurements under ponding conditions are becoming largely applied techniques for an approximate characterization of crusted soils. In this study, the impact of crusting on soil hydraulic conductivity was assessed in a Mediterranean vineyard (western Sicily, Italy) under conventional tillage. The BEST (Beerkan Estimation of Soil Transfer parameters) algorithm was applied to the infiltration data to obtain the hydraulic conductivity of crusted and uncrusted soils. Soil hydraulic conductivity was found to vary during the year and also spatially (i.e., rows vs. inter-rows) due to crusting, tillage and vegetation cover. A 55 mm rainfall event resulted in a decrease of the saturated soil hydraulic conductivity, Ks, by a factor of 1.6 in the inter-row areas, due to the formation of a crusted layer at the surface. The same rainfall event did not determine a Ks reduction in the row areas (i.e., Ks decreased by a non-significant factor of 1.05) because the vegetation cover intercepted the raindrops and therefore prevented alteration of the soil surface. The developed ring insertion methodology on crusted soil, implying pre-moistening through the periphery of the sampled surface, together with the very small insertion depth of the ring (0.01 m), prevented visible fractures. Consequently, Beerkan tests carried out along and between the vine-rows and data analysis by the BEST algorithm allowed to assess crusting-dependent reductions in hydraulic conductivity with extemporaneous measurements alone. The reliability of the tested technique was also confirmed by the results of the numerical simulation of the infiltration process in a crusted soil. Testing the Beerkan infiltration run in other crusted soils and establishing comparisons with other experimental methodologies appear advisable to increase confidence on the reliability of the method that seems suitable for simple characterization of crusted soils.