This chapter explores the ongoing crisis in the Cypriot cruise industry amidst digitisation. Analysis draws on research workshops and in-depth interviews with government officials, port authorities, cruise companies, suppliers and other stakeholders. The findings reveal a number of wrongdoings, resulting in a decade-long decline. Also, the findings communicate the latest institutional attempts, aiming to help the industry adapt and recover, within an EU-wide framework of digitisation. By examining the implementation of a National Maritime Single Window (NMSW) and its harmonisation through the European Maritime Single Window (EMSW), we introduce a platform called ‘NAYS’, which aims at facilitating a more inclusive and sustainable supply chain. The study makes an original contribution to literature on system interoperability and utilisation of shipping information in the cruise industry.