Phylogenetic reconstruction of the Greater Antillean genera Coeloneurum , Espadaea, Goetzea, and Henoonia was carried out using DNA sequence data from the chloroplast regions rbcL, ndhF, trnL intron, trnL/F spacer, as the well as the nuclear ITS region, totaling over 5,000 base pairs. One of the objectives of the study was to test the monophyly of these Antillean genera, and to elucidate their relationships with the subfamilies of the Solanaceae. The phylogeny was also applied in the assessment of trends of morphological and ecological evolution. Our results demonstrate the monophyly of the Greater Antillean genera, but they are part of a larger clade with two basal lineages endemic to South America: Duckeodendron and Metternichia. This larger clade is clearly within the Solanaceae, as one of the first lineage splits of the family. We propose the creation of the monophyletic subfamily Goetzeoideae, which includes the Greater Antillean genera and the South American Duckeodendron and Metternichia. Pollen morphology shows congruence with the relationships outlined by the molecular phylogeny. The phylogeny indicates that there has been a shift in the ecology of this group, from wet-mesic environments, to xeric conditions. In addition, there has been a shift in the pollination syndrome, from nocturnal visitation by insects to ornithophily.