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Oceanic islands have long been considered engines of differentiation and speciation for terrestrial organisms. Here we investigated colonisation and radiation processes in the Madeira Archipelago and the Canary Islands of the Andrena wollastoni group of bees (subgenus Micrandrena), which comprises six endemic species and five endemic subspecies on the islands. Mitochondrial COI sequences support the monophyly of the four species of the Canary Islands and the two species of the Madeira Archipelago and suggest a relatively young age for all taxa. The data do not support a simple stepping-stone model (eastern-western colonisation from the mainland, with splitting into new taxa), but suggest Andrena gomerensis (extant on La Gomera and La Palma) or its ancestor as the basal lineage from which all other taxa evolved. Andrena lineolata (Tenerife) or its putative ancestor (A. gomerensis) is sister to A. dourada (Porto Santo), A. catula (Gran Canaria), and A. acuta (also Tenerife). Andrena dourada (Porto Santo) and A. wollastoni (Madeira Island) are sister species. Morphologically and morphometrically defined subspecies were not distinguishable with COI DNA sequences. Colonisation likely led from the Canary Islands to the Madeira Archipelago and not from the mainland directly to the latter.