The Grenadine Islands in the southern Lesser Antilles have received relatively little attention by archaeologists compared to other regions of the Caribbean. However, research over the last ten years on Carriacou, the largest and southernmost island in the Grenadines, has significantly improved our understanding of when these islands were settled in prehistory and subsequent cultural changes that occurred from ca. AD 400 to 1400. An extension of this research project into the smaller islands of Mustique and Union in May 2010 has now provided preliminary data with which Carriacou and other nearby islands such as St. Vincent and Grenada can be compared. Here we provide a description of the sites we investigated and present analysis of recovered archaeological remains through subsurface testing. This represents the first concerted effort by archaeologists since the 1970s to investigate the Grenadines and also reports a new site on Mustique known as Lagoon Bay. Results of this and previous research demonstrates that numerous villages developed in the Grenadines during the terminal Saladoid period and fluoresced shortly thereafter during the Troumassoid period (ca. AD 600 - 1300). Preliminary analysis of materials recovered, including pottery and mollusks, as well as several new radiocarbon dates, provide a framework for guiding future research at these sites, most of which are threatened by development, agricultural activities, and/or erosion.