The volcanic archipelago of the Canary Islands, 100 km off the northwestern coast of Africa, harbors 43 endemic species of the mostly circum-Mediterranean spider genus Dysdera (Araneae, Dysderidae). This amounts to approximately one-fourth of all known Dysdera species in an area that represents 0.1% of the range of the genus. In order to address the origin of this extraordinary number of endemic species, the phylogenetic relationships among all the endemic taxa and a sample of 27 continental species were reconstructed. A simultaneous cladistic analysis was performed on 66 morphological characters, 471 bp of the cytochrome oxidase I and 424 bp of the 16S rRNA mitochondrial genes. The preferred most parsimonious tree supports a single origin for most of the endemic species (84%), although this tree is ambiguous regarding the total number of overseas colonizations (allowing a minimum of two and a maximum of four colonization events). Our data suggest that the Canary Islands have been the source of the colonizers of some of the remaining Macaronesian archipelagoes (certainly for the Selvagem Islands and the Cape Verdes and possibly for Madeira); the Azores have been independently colonized by dysderids from the continent. The present study provides a phylogenetic framework for an exceptional case of insular species radiation, an essential tool for unraveling the factors that have promoted this amazing diversification. Species radiations in oceanic archipelagoes are excellent models for the study of speciation processes.