Health Literacy (HL) is an important health determinant: low HL skills result in less healthy choices, riskier behavior, poorer health, less self-management and more hospitalization. An observational study was conducted in a selected population, attending the waiting rooms of family general practitioners, with the aim of assessing HL capabilities through the administration of two HL screeners (IMETER and SILS-IT), and comparing the two measures. An anonymous questionnaire was administered, consisting of the Italian versions of the two tests on a single sheet. Demographic data, as well as concomitant chronic diseases and vaccines received, were also collected. HL skills were measured by the scores observed at both tests, and by the frequency of subjects with low HL levels according to the respective cut-off values. Overall, 305 questionnaires were collected and analyzed. Regarding IMETER, the observed frequency of subjects with low HL skills was 25.2% and the mean score and mean adjusted-score (26.3 ± 8.8 and 23.2 ± 9.4, respectively) were lower than those observed in previous studies. Similarly, at SILS-IT the percentage of subjects with low skills (49.9%) was higher than observed previously. IMETER showed high internal consistency (Cronbach's alpha > 0.9). The two measures were significantly correlated, although with a low Spearman's coefficient, and IMETER did not provide significant information about the probability to predict low HL according to SILS-IT. These results are explainable by the differences in assessment and domains between the two tests, both reliable and suitable to screen patients with low functional HL.