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Unregulated built-up area expansion is a typical practice in Greece mostly on the islands, it is driven by the mass tourism development and the demand for second houses. Significant social, economic and environmental issues are linked to this practice. Santorini, a Greek island – which is characterized by important natural and cultural heritage properties and intense tourist development – is chosen here for the empirical part of the study. This paper attempts to study and quantify both the unregulated built-up area expansion and its impact on the natural and cultural environment. The intense ex-urban built-up area expansion that takes place on Santorini is interpreted on the basis of the Greek spatial planning framework so that its weaknesses that emerge will address the issue. [ABSTRACT FROM AUTHOR]