The Cycadales are a group of significant global conservation concern and have the highest extinction risk of all seed plants. Understanding the synchronisation of reproductive phenology of Cycadales may be useful for conservation by enabling the targeting of pollen and seed collection from wild populations and identifying the window of fertilisation to aid in the cultivation of Cycadales. Phenological data for 11 species of Zamia were gathered from herbarium specimens. Four phenological characters were coded with monthly character states. DNA was isolated and sequenced for 26S, CAB, NEEDLY, matK and rbcL, and a simultaneous phylogenetic analysis of phenology and DNA sequence data was carried out. Three major clades were recovered: a Caribbean clade, a Central American clade and a South American clade. Eight species showed statistically significant synchronisation in microsporangiate and ovulate phenological phases, indicating the time of fertilisation. Close reproductive synchronisation was consistently observed throughout the Caribbean clade (statistically significant in four of five species) but was less consistent in the Central American clade (statistically significant in one of two species) and South American clade (statistically significant in three of four species). Ultimately, phenology is shown to be a potential driver of speciation in some clades of Zamia and in others to be a potential barrier to hybridisation.