Our article discusses the shifting cultural relationships between Kos and the Greek mainland during the Late Bronze Age and the first part of the Early Iron Age (EIA). To do so, we examine the urban and funerary landscapes at the sites of the “Serraglio”, Eleona, and Langada. As cultural proxies, built environments and mortuary arenas are conservative elements, which, when transformed, imply relevant socio-cultural changes. On Kos, during the periods considered, transitions in these elements occurred to varying degrees, providing an ideal framework for examining the internal developments and external interactions that impacted local cultural dynamics. After a brief overview of the Koan sites, we introduce our theoretical background. We then propose a new interpretative framework to measure shifts in Koan urban and funerary landscapes. Our freshly coined approach defines cycles of punctuated transitions, followed by gradual transitions and stability periods. For each cycle, we recognize changes using two analytical tools, which we term layout and stage. The former captures shifts in structural orientation, organization, and size, while the latter includes major actions, such as the foundation, functional transformation, and abandonment of a given site. Even if this theoretical framework is born out of our analysis of the Koan trends, we believe that it can be successfully applied to cultural transitions from other areas and/or different time periods. Our survey and discussion of the evidence identify six transitional cycles on Kos between the seventeenth and the tenth century BC. The most profound changes occurred after Late Helladic IIIA2 and the Middle Protogeometric phase, when we observe contemporary shifts in the layout and stage of the urban and funerary landscapes around the “Serraglio”. These shifts correspond to transformations in the projected identities of the Koan community, with a significant incorporation of Mycenaean and EIA Greek mainland features in the local socio-cultural arena.