Peripheral artery disease (PAD) increases the risk of diabetes, while diabetes increases the risk of PAD, and certain symptoms in each disease increase the risk of contracting the other. This review aims to shed light on this harmful interplay between the two disorders, with an emphasis on the phenotype of a patient with both diabetes and PAD, and whether treatment should be individualized in this high-risk population. In addition, current guideline recommendations for the treatment of PAD were analyzed, in an attempt to establish the differences and evidence gaps across a population suffering from these two interconnected disorders.