Purpose – For many wineries, internationalisation strategies, particularly in the form of exports may provide opportunities and financial gains. However, as more wine producers enter and compete in an increasingly convoluted wine market, accordingly the “playing field” in the wine industry becomes increasingly complex. To shed more light into wineries’ internationalisation efforts through exports in the currently uncertain business climate, this preliminary study investigates a group of predominantly micro, small, and medium wineries from both New and Old Worlds of wine. The paper aims to discuss these issues. Design/methodology/approach – An online questionnaire was designed to gather data from winery owners and managers that invited to participate voluntarily in the study; a total of 499 usable responses were obtained. Findings – Diversifying and entering new markets, especially due to domestic competition are respondents’ main reasons for embarking in exports, while unfavourable currency exchange, issues of trust, or entry barriers are key challenges many of them face. Further, despite the relatively limited wine production of most participating wineries, respondents perceive a necessity to be present internationally. Indeed, rather than fitting into a specific business model/cycle, the current complex business environment is triggering export strategies among entrepreneurs. Originality/value – The fiercely competitive wine market and continuously changing consumer trends significantly contribute to the complexities the wine industry faces. However, few academic studies have investigated some of the complexities that wineries located in different geographic, economic, political, and social environments face. In this regard, the study makes a contribution by identifying several developments related to complexity theory, including the impacts of globalisation, competition, and change, and the resulting complexity in the wine sector.