The Archipini fauna of the Caribbean is revised to include 33 species. Most previously described species occurring in the region are redescribed and figured. Fourteen new species are described, three new combinations are presented, and six new synonymies are proposed. In addition, previously unplaced Neotropical species (i.e. “Archipini unplaced”) are assigned to genera. This results in one new genus, seven new combinations, and two additional new synonymies. Males of three species and females of two species are described for the first time. The concept of Claduncaria Razowski is expanded and given a new diagnosis. A unique external sexual coupling mechanism in Claduncaria is proposed and discussed. Genus and species keys, distribution maps, a regional checklist, Neighbor-joining and Maximum Likelihood trees based on COI barcode sequence data are provided. Phylogenetic relationships among Caribbean Archipini are briefly discussed.