The main purpose of this paper is searching for answers to the almost enthusiastic support of the Portuguese State for Turkey’s accession to the European Union. The diplomatic position of Portugal is intriguing since both states are historically unfamiliar one to another—not only for their geography (Portugal is an Atlantic country and Turkey a Mediterranean and Middle Eastern one) but, despite NATO, for their little political or economic interaction. To enquire into this subject, a neorealist approach and a qualitative methodology were chosen. The concept and theory of small states and group thinking are also part of the analytical framework. Thus, an analysis of foreign policy and diplomatic documents, both of the Portuguese State and the Turkish State, were made, as well as public declarations of their rulers. Additionally, a review of the scarce literature about the subject was carried out. The analysis focused mainly in the last twenty years, when Turkey became candidate for accession to the European Union and negotiations were opened.