The evolution of secondary (insular) woodiness and the rapid disparification of plant growth forms associated with island radiations show intriguing parallels between oceanic islands and tropical alpine sky islands. However, the evolutionary significance of these phenomena remains poorly understood and the focus of debate. We explore the evolutionary dynamics of species diversification and trait disparification across evolutionary radiations in contrasting island systems compared to their non‐island relatives. We estimate rates of species diversification, growth form evolution, and phenotypic space saturation for the classical oceanic island plant radiations – the Hawaiian silverswords and Macaronesian Echium ‐ and the well‐studied sky island radiations of Lupinus and Hypericum in the Andes. We show that secondary woodiness is associated with dispersal to islands and with accelerated rates of species diversification, accelerated disparification of plant growth forms, and occupancy of greater phenotypic trait space for island clades than their non‐island relatives, on both oceanic and sky islands. We conclude that secondary woodiness is a prerequisite that may act as a key innovation, manifest as the potential to occupy greater trait space, for plant radiations on island systems in general, further emphasizing the importance of combinations of clade‐specific traits and ecological opportunities in driving adaptive radiations.