Humans residing or working in cold environments exhibit a stronger cold-induced vasodilation (CIVD) reaction in the peripheral microvasculature than those living in warm regions of the world, leading to a general assumption that thermal responses to local cold exposure can be systematically improved by natural acclimatization or specific acclimation. However, it remains unclear whether this improved tolerance is actually due to systematic acclimatization, or alternately due to the genetic predisposition or self-selection for such occupations. Longitudinal studies of repeated extremity exposure to cold demonstrate only ambiguous adaptive responses. In field studies, general cold acclimation may lead to increased sympathetic activity that results in reduced finger blood flow. Laboratory studies offer more control over confounding parameters, but in most studies, no consistent changes in peripheral blood flow occur even after repeated exposure for several weeks. Most studies are performed on a limited amount of subjects only, and the variability of the CIVD response demands more subjects to obtain significant results. This review systematically surveys the trainability of CIVD, concluding that repeated local cold exposure does not alter circulatory dynamics in the peripheries, and that humans remain at risk of cold injuries even after extended stays in cold environments.