Species in Mimulus section Erythranthe (monkeyflowers) have become model systems for the study of the genetic basis of ecological adaptations. In this study, we pursued two goals. First, we reconstructed the phylogeny of species in Erythranthe using both DNA sequences from the ribosomal DNA ITS and ETS and AFLPs. Data from rDNA sequences support the monophyly of the section, including M. parishii, but provide little support for relationships within it. Analyses using AFLP data resulted in a well-supported hypothesis of relationships among all Erythranthe species. Our second goal was to reconstruct ancestral pollination syndromes and ancestral states of individual characters associated with hummingbird-pollinated flowers. Both parsimony and likelihood approaches indicate that hummingbird pollination evolved twice in Erythranthe from insect-pollinated ancestors. Our reconstruction of individual characters indicates that corolla color and some aspects of corolla shape change states at the same point on the phylogenetic tree as the switch to hummingbird pollination; however, a switch to secretion of high amounts of nectar does not. Floral trait transformation may have been more punctuational than gradual.