The weevil genus Pachnaeus Schoenherr, 1826 (Coleoptera: Curculionidae: Entiminae: Eustylini Lacordaire) is revised to accommodate 21 species, including the following 10 new species from the northern Caribbean region: Pachnaeus andersoni sp. nov. (Little Cayman), Pachnaeus eisenbergi sp. nov. (Jamaica), Pachnaeus godivae sp. nov. (Cayman Brac), Pachnaeus gordoni sp. nov. (Jamaica), Pachnaeus howdenae sp. nov. (Bahamas), Pachnaeus ivieorum sp. nov. (Bahamas with adventive records from Florida), Pachnaeus maestrensis sp. nov. (Cuba), Pachnaeus morelli sp. nov. (Haiti), Pachnaeus obrienorum sp. nov. (Cuba and Bahamas), and Pachnaeus quadrilineatus sp. nov. (Jamaica).Pachnaeus can be distinguished from similar, co-occurring taxa such as Exophthalmus quadrivittatus (Olivier, 1807), Exophthalmus roseipes (Chevrolat, 1876), Exophthalmus vittatus (Linnaeus, 1758), and Diaprepes abbreviatus (Linnaeus, 1758) by (1) the presence of postocular vibrissae, (2) endophallus primarily membranous and sac-like proximally, and long (>3 × width), tubular, and sclerotized distally, (3) additional endophallic sclerites typically absent, (4) a never bicarinate, typically tricarinate, rostrum, and several additional characteristics of the pedon, endophallus, pronotal structure, rostral structure, and scaling. Based on these characters, Pachnaeus sommeri (Munck af Rosenschoeld in Schoenherr, 1840) comb, nov. and Pachnaeus gowdeyi (Marshall, 1926) comb. nov. are transferred into the genus from Exophthalmus Schoenherr and Lachnopus Schoenherr respectively. This revision provides genus and species redescriptions, diagnoses, illustrations, and the first comprehensive key to all 21 species within the present circumscription of Pachnaeus, in addition to reviewing the known biology and observed intraspecific variation within species. The complex taxonomic history of the genus is reviewed, and the evolutionary relationships of its presumed constituent clades are proposed through the construction of informal species groups and subgroups based on diagnosable shared traits. Lectotypes for Pachnaeus citri Marshall, Pachnaeus costatus Perroud, and Exophthalmus sommeri Munck af Rosenschoeld in Schoenherr and paralectotypes of P. citri (3 specimens) and E. sommeri (4 specimens) are designated. New state and national records are reported for Pachnaeus azurescens Gyllenhal in Schoenherr for Florida, U.S.A. and new national records are reported for Pachnaeus litus (Germar) for the Bahamas. Validity of the names Docorhinus Schoenherr, 1823 and Pachnaeus Schoenherr, 1826 is treated. Generic placement of Pachnaeus roseipes Chevrolat, 1876 is explored.