Since our knowledge of the greater part of the Tipulidae of the Canary Islands, Madeira and the Azores is poor, the types of most species described from these islands have been studied, and critical species are redescribed. One new species, Limonia (Dicranomyia) michaeli n.sp. is described, and a list of all known species is provided. The taxonomic and distributional data suggest that Tipulidae arrived on these islands in three invasion waves, viz. a first in early Tertiary, a second in late Tertiary and a third in more recent times. Species that came in the first wave either colonized Madeira and the Azores or the Canary Islands, the second wave only, colonized Madeira and the Canary Islands, and the third invasion finally reached the Canary Islands only.