We examined whether expertise effects are present in cutaneous wind perception. To this end, we presented wind stimuli consisting of different wind directions and speeds in a wind simulator. The wind simulator generated wind stimuli from 16 directions and with three speeds by means of eight automotive wind fans. Participants were asked to judge cutaneously perceived wind directions and speeds without having access to any visual or auditory information. Expert sailors (n = 6), trained to make the most effective use of wind characteristics, were compared to less-skilled sailors (n = 6) and to a group of nonsailors (n = 6). The results indicated that expert sailors outperformed nonsailors in perceiving wind direction (i.e., smaller mean signed errors) when presented with low wind speeds. This suggests that expert sailors are more sensitive in picking up differences in wind direction, particularly when confronted with low wind speeds that demand higher sensitivity.