This paper explores tourism development in the Kaliningrad Oblast associated with European Union (EU) enlargement. Although politically part of the Russian Federation, Kaliningrad now exists as an exclave, distant from the Russian border and surrounded by EU territory. Situated in discourse on cross-border tourism, this paper argues for a more active analysis of the geopolitics of tourism. Kaliningrad's future is intricately linked with the possible re-establishment of a former tourism region along the southeastern Baltic coast which crosses several state borders. The potential for this to be achieved, however, is a function of the resolution of the strategic interests of neighbouring states and the EU.