Recent advances in ecological niche modeling (ENM) algorithms, in conjunction with increasing availability of geographic information system (GIS) data, allow species' niches to be predicted over broad geographic areas using environmental characteristics associated with point localities for a given species. Consequently, the examination of how niches evolve is now possible using a regionally inclusive multivariate approach to characterize the environmental requirements of a species. Initial work that uses this approach has suggested that niche evolution is characterized by conservatism: the more closely related species are, the more similar are their niches. We applied a phylogenetic approach to examine niche evolution during the radiation of Cuban trunk-ground anoles (Anolis sagrei group), which has produced 15 species in Cuba. We modeled the niche of 11 species within this group using the WhyWhere ENM algorithm and examined the evolution of the niche using a phylogeny based on approximately 1500 base pairs of mitochondrial DNA. No general relationship exists between phylogenetic similarity and niche similarity. Examination of species pairs indicates some examples in which closely related species display niche conservatism and some in which they exhibit highly divergent niches. In addition, some distantly related species exhibit significant niche similarity. Comparisons also revealed a specialist-generalist sister species pair in which the niche of one species is nested within, and much narrower than, the niche of another closely related species.