The rapid development of digital technologies in recent years and the exponential growth of computing power and storage capacity of "wise machines" lead inevitably to the increasingly important role of artificial intelligence (AI) in many fields of activity, including maritime transport [1, 2]. These developments, combined with growing global challenges, give us reason to believe that, if not in the coming years, then in the coming decades, we definitely will face major changes in the world in general and in maritime affairs in particular. They, among other things, will force us to abandon the beliefs and paradigms that have so far seemed to be "waterproof." Before discussing in a practical way the problem posed in the title of this paper, it is essential to ask some to a certain extent philosophical questions, which inevitably arise when analyzing this topic and which cause a slight dissonance in the author. There may not be (or even cannot be found at all) good answers to these questions, especially within the scope of single paper, but defining these questions and "bringing them into play" seems important to the author of the paper. The first question is what we mean by talking about something or someone "smart" (smart person, smart behavior, smart economic, smart shipping, or even smart education). It is clear that the answers to the question about the "smartness" of the listed objects and subjects, even if they could be found, would differ significantly from each other. The author of this paper does not attempt and even probably is not able to give an exhaustive definition of "smart" for all these objects and subjects (and possible many others). However, the author would like to clarify what he