Intensified archaeological research in the Caribbean over the past 2 decades has provided a wealth of new information on how and when these islands were settled prehistorically. However, there has been a paucity of research on islands in the southern Lesser Antilles, which would allow for more rigorous testing of migration models and various settlement pattern hypotheses. To address some of these chronological and geographical gaps, we present a corpus of 41 radiocarbon dates from several sites in the Grenadine Island chain. Results to date support a relatively late Ceramic Age settlement of these smaller islands (about AD 400) compared to other nearby, larger islands in the southern Lesser Antilles (about AD 200) as well as the Caribbean as a whole (about 400/500 BC). Intriguing questions also remain as to an apparent, but as yet inadequately tested, pattern where earlier colonization dates are correlated with larger island size.