Rapateaceae (16 genera, approximately 100 species) is largely restricted to the tepuis and sandplains of the Guayana Shield in northern South America, with Maschalocephalus endemic to West Africa. The family has undergone extensive radiation in flower form, leaf shape, habit, and habitat. To analyze the evolution of these distributions and traits, we derived a molecular phylogeny for representatives of 14 genera, based on sequence variation in the chloroplast-encoded ndhF gene. The lowland subfamily Rapateoideae is paraphyletic and includes the largely montane subfamily Saxofridericioideae as a monophyletic subset. Overall, the morphological/anatomical data differ significantly from ndhF sequences in phylogenetic structure, but show a high degree of concordance with the molecular tree in three of four tribes. Branch lengths are consistent with the operation of a molecular clock. Maschalocephalus diverges only slightly from other Monotremae: it is the product of relatively recent, long-distance dispersal, not continental drift--only its habitat atop rifted, nutrient-poor sandstones is vicariant. The family appears to have originated approximately 65 Mya in inundated lowlands of the Guayana Shield, followed by: (1) wide geographic spread of lowland taxa along riverine corridors; (2) colonization of Amazonian white-sand savannas in the western Shield; (3) invasion of tepui habitats with frequent speciation, evolution of narrow endemism, and origin of hummingbird pollination in the western Shield; and (4) reinvasion of lowland white-sand savannas. The apparent timing of speciation in the Stegolepis alliance about 6-12 Mya occurred long after the tepuis began to be dissected from each other as the Atlantic rifted approximately 90 Mya. Given the narrow distributions of most montane taxa, this suggests that infrequent long-distance dispersal combined with vicariance accounts for speciation atop tepuis in the Stegolepis alliance.