The current study presents the results of the first dendrochronological survey performed over the East Aegean island of Symi. Research Highlights: Dendrochronological research of the East Aegean region is of paramount importance since dendrochronological data from the region, and especially the islands, are still limited. Background and Objectives: The main aim of the study is to explore the dendrochronological potential of the island, focusing on the dating of historical wood and buildings as well as dendroprovenancing. Materials and Methods: A total of 57 wood samples were collected from historical timber from windmills and architectural elements, including doors and warehouse planks, while 68 cores were collected from the three dominant tree species of the island—Cupressus sempervirens, Pinus brutia, and Quercus ithaburensis subsp. macrolepis—in an attempt to develop local reference chronologies that could be useful in dating historical timber Results: Of the historical timber, at least nine different species have been detected, with conifers representing the majority of the collected material. In total, 56% of the dendroarchaeological samples, belonging to four different species, were dated absolutely. According to cross-dating and dendroprovenancing results, Pinus nigra, Cedrus sp., and Quercus sp. represent timber imported from present-day Turkey while the fir samples collected from the windmills originate from Central Europe. The use of local timber is also highly probable although it could not be confirmed by the reference chronologies developed for the three dominant tree species of the island. Conclusions: The results of the study reveal the dendrochronological potential of the island from both dendroarchaeological and dendroecological perspectives. The finding that most of the wood was imported mainly from Turkey highlights the importance of timber trade with the Turkish mainland during the mid-18th and 19th centuries. Chronologies developed from living trees could be used in future studies for dating historical material while further research would increase our understanding of past timber trade and the island’s history.