We analysed the geographical origins and divergence times of the West Indian hummingbirds, using a large clock-dated phylogeny that included 14 of the 15 West Indian species and statistical biogeographical reconstruction. We also compiled a list of 101 West Indian plant species with hummingbird-adapted flowers (90 of them endemic) and dated the most species-rich genera or tribes, with together 41 hummingbird-dependent species, namely Cestrum (seven spp.), Charianthus (six spp.), Gesnerieae (75 species, c. 14 of them hummingbird-pollinated), Passiflora (ten species, one return to bat-pollination) and Poitea (five spp.), to relate their ages to those of the bird species. Results imply that hummingbirds colonized the West Indies at least five times, from 6.6 Mya onwards, coming from South and Central America, and that there are five pairs of sister species that originated within the region. The oldest of the dated plant groups diversified 9.1, 8.5, and 5.4 Mya, simultaneous with or slightly before the extant West Indian bird radiations. The time frame of the coevolved bird/flower mutualisms obtained here resembles that recently inferred for North America, namely 5–9 Mya.