The Hawaiian archipelago is often cited as the premier setting to study biological diversification, yet the evolution and phylogeography of much of its biota remain poorly understood. We investigated crab spiders (Thomisidae, Mecaphesa) that demonstrate contradictory tendencies: (i) dramatic ecological diversity within the Hawaiian Islands, and (ii) accompanying widespread distribution of many species across the archipelago. We used mitochondrial and nuclear genetic data sampled across six islands to generate phylogenetic hypotheses for Mecaphesa species and populations, and included penalized likelihood molecular clock analyses to estimate arrival times on the different islands. We found that 17 of 18 Hawaiian Mecaphesa species were monophyletic and most closely related to thomisids from the Marquesas and Society Islands. Our results indicate that the Hawaiian species evolved from either one or two colonization events to the archipelago. Estimated divergence dates suggested that thomisids may have colonized the Hawaiian Islands as early as ~10 million years ago, but biogeographic analyses implied that the initial diversification of this group was restricted to the younger island of Oahu, followed by back-colonizations to older islands. Within the Hawaiian radiation, our data revealed several well-supported genetically distinct terminal clades corresponding to species previously delimited by morphological taxonomy. Many of these species are codistributed across multiple Hawaiian Islands and some exhibit genetic structure consistent with stepwise colonization of islands following their formation. These results indicate that dispersal has been sufficiently limited to allow extensive ecological diversification, yet frequent enough that interisland migration is more common than speciation.