The Cuban species of Calisto are reviewed based on the morphology of adult and immature stages, as well as DNA sequences of six genes (COI, EF1α, wingless, GAPDH, RpS5, CAD). A new species, Calisto occulta sp. n., is described from the northeastern Cuban mountains. Calisto smintheus Bates, 1935 and C. bruneri, Michener 1949 are revised and revalidated. A new status, the species level, is proposed for C. brochei, Torre 1973, C. muripetens, Bates 1939 and C. bradleyi, Munroe 1950. The immature stages of C. smintheus, C. brochei, and C. occulta are described for the first time, and those of C. herophile, Hübner 1823 are redescribed. Useful morphological characters for adults are the shape and conspicuousness of androconial patch, the number and relative size of white dots on underside of hindwing, the shape of aedeagus, the shape of digitiform projection of genitalia valve, the shape and relative size of tegumen and uncus, the relative size of female genitalia, the height of sterigmal ring dorsal crown of the latter, and the relative size of corpus bursae and ductus bursae. For the immature stages, the most important characters are the color pattern of head capsule, the number and width of longitudinal lines of body, in the larvae; and the color pattern and the absence or presence of dorsal ridges on the abdomen of pupae. The phylogenetic relationships between the Cuban Calisto species are quite robust and well-supported; however, conflict between mitochondrial and nuclear datasets was detected in C. brochei, C. muripetens and to a lesser degree in C. bradleyi.