Islands played a key role in Charles Darwin's observations and experiments on plant dispersal. By means of these experiments, he expunged the old idea that a given species could originate at multiple times and in multiple places. More importantly, by seeing the capabilities for dispersal of plant seeds, fruits and branches, he was able to develop ideas of how plants reach islands and thus he is one of the founders of plant biogeography. For facts regarding floristic distribution of plants, Darwin relied on other workers, most notably Sir Joseph Dalton Hooker. Among his insights were the differences between oceanic and continental islands on a floristic basis, ideas on how age of island and distance from mainland areas influenced composition of island floras, the nature of endemism on islands and the role islands and archipelagos served as stepping stones in dispersal. Ingenious at proposing hypotheses, but always respectful of facts, Darwin sought explanations for plant adaptations on islands at a time when knowledge of island botany was little more than floristic in nature. These explanations are compared with selected recent works in island botany. © 2009 The Linnean Society of London, Botanical Journal of the Linnean Society, 2009, 161, 20–25.