During the last years Foreign Direct Investments (FDI) have rapidly increased in Eastern European Countries. Bulgaria, even though it presents a turbulent environment, receives increasing flows of FDI. This research will examine FDI in Bulgaria from the perspective of a week economy, the economy of Greece. The purpose of this study is to explore the internationalization process of a Greek Small Medium Enterprise (SME) investing in Bulgaria. In order to achieve the research’s objectives, a single case study was employed. In particular the motives and barriers were examined as well as the future prospects of the investment. The findings came as a result of applying the eclectic model developed by Dunning, on the internationalisation attempt of the researched company. SMEs have inherent characteristics that affect their internationalisation behaviour. This study can be a useful source of information for anyone that wishes to gain an insight on the internationalization process of a Small Medium Enterprise investing in a turbulent environment.