Determining how to operate in foreign markets is challenging for the performing arts (PA) because the particular nature of their activities necessarily entails sustainable complexities. This study aims to extend understanding of the internationalization of PA to shed light on the strategic decisions adopted by cultural agents to achieve an economic and cultural objective—generating international income while ensuring the symbolic value of cultural products rooted in local values. A longitudinal empirical case of one leading enterprise in international flamenco production with a successful history in international markets is reported here, and in-depth insights into four strategic decisions that can boost the sustainable internationalization of PA are gained: why (motivations), what (product), where (market selection), and how (entry modes). The results have theoretical and practical implications for a cultural sector with few examples of internationalization that is seeking for international markets to become sustainable while being subject to public financing cuts, strong competition, and globalization. The important role of intermediaries in bridging the gaps between different actors of the PA value chain and in assuring sustainable cultural management of the internationalization process is also identified.