The large daisy tribe Gnaphalieae occurs in extra-tropical habitats worldwide, but is most diverse in southern Africa and in Australia. We explore the age and evolutionary history of the tribe by means of a phylogenetic hypothesis based on Bayesian analysis of plastid and nuclear DNA sequences, maximum likelihood reconstruction of ancestral areas, and relaxed Bayesian dating. Early diversification occurred in southern Africa in the Eocene-Oligocene, resulting in a grade of mostly Cape-centred lineages which subsequently began speciating in the Miocene, consistent with diversification times for many Cape groups. Gnaphalieae from other geographic regions are embedded within a southern African paraphylum, indicating multiple dispersals out of southern Africa since the Oligocene to Miocene which established the tribe in the rest of the world. Colonisation of Australia via direct long-distance trans-oceanic dispersal in the Miocene resulted in the radiation which produced the Australasian gnaphalioid flora. The similarly diverse regional gnaphalioid floras of Australasia and southern Africa thus exhibit very different temporal species accumulation histories. An examination of the timing and direction of trans-Indian Ocean dispersal events in other angiosperms suggests a role for the West Wind Drift in long-distance dispersal eastwards from southern Africa.