The thesis applies a modification of the concept of landscape to embody physical settings, social behaviour and affixed meanings. The argument focuses on both how a specific environment was created as well as perceived on four Estonian islands from the late seventeenth century until the present. Islands have clear natural boundaries, and thus they comprise well-defined entities. Physical environment is seen as an important factor in the formation of home and identity. Island life in Estonia was on the background of complicated power relations dominated by foreign ruling classes less restricted, and historically the islanders had better opportunities for gaining a livelihood. They were thus part of a common Baltic Sea world often passed by in native Estonian research, which has concentrated on mainland farming traditions. Living conditions on the islands were drastically changed by Soviet occupation after the Second World War when they came to belong to the strictly regulated border area towards the West. The occupation is seen as a focal point of the thesis lending it a before and after perspective. The local variation was great and therefore island communities and landscapes are critically examined in a long-term perspective focusing on settlement history, the outward signs of belonging to a place (kinship, way of doing things, skills, dialect, humour, traditions) and on landscape biography. It is argued that constant change was accommodated in the mental picture, but an abrupt one caused an idealisation of national cultural values. The mythical elements are examined after first establishing the content of the islescapes of home and of popular islescapes of the 1930s. At present, people are in the process of renewing contacts and revising their islescapes of memory and imagination into possible futures.