Seven new species and one new subspecies of Helicopsyche von Sieboid are described from Cuba, Hispaniola, and Puerto Rico based on adults; additionally four species and one subspecies belonging to the fauna of these islands are redescribed. Both sexes are described when correct association of females is possible. Considerations are made on the value of different characters in discriminating species in this genus. Presently 10 taxa are known from Cuba, 5 from Hispaniola, 4 from Puerto Rico (and 3 from Jamaica). An attempt is made to establish the affinities of these species. The West Indian Helicopsyche represent one of the richest assemblages of this genus in the world fauna.