This paper explores the socio-economic and cultural transitions of Bozcaada, a small Turkish island in northern Aegean Sea, with a focus on seasonal changes. The local economy of the island has shifted from small-scale viniculture to domestic tourism over the last three decades. Currently, the local economy became dominated by domestic tourism businesses. Alongside this major change, the socio-cultural structure of the island has started to change with in-migration of middle-class urbanites. Although tourism enabled the local population to remain in the location in the light of the downfall of small-scale agricultural practices, it also brought about an unusual pattern of seasonal migration: temporary out migration of the static residents. Almost three quarter of the registered population on Bozcaada move to city centres in winter which is off-season for the local tourism. This not on only interrupts the socio-economic and socio-cultural life of the island but also put the local services in danger.