Drama surrounds the decision to build a cruise berthing facility in the Cayman Islands. After two decades waiting in the wings, the berthing is the most extensive infrastructure plan and the most divisive project Cayman has ever considered. Cruise passengers must wait for their ship to anchor offshore and board a tender to carry them to the port. The Government intended to improve this situation by building a cruise berthing alongside a total redevelopment of its cargo port through a contractual public-private partnership. The project was awarded to a consortium led by Carnival and Royal Caribbean, but various decisions have been kicked back until after the May 2021 elections. However, has the ship now sailed? This article’s goal is to provide a way forward to overcome the current deadlock. The article is structured in three main sections: a general section on cruise ship tourism in Cayman to put this case study in context; the second section is a critical assessment of the cruise berthing’s timeline and milestones; and the third section assesses its impact on the host community. Desk-based research blending international and local bibliography provides a uniquely local perspective.