Vacations and leisure activities constitute an important part of human life. Nowadays, a lot of attention is paid to cruising, that is reported to be a favourite vacation choice for families with kids and for Millenials. Like other distributed events (events that gather multiple activities distributed in space and time under one umbrella) such as big festivals, conventions, conferences etc., cruises offer a vast variety of simultaneous on-board activities for all ages and tastes. This results in a cruiser's information overload, in particular given a very limited availability of activities. Recommender systems appear as a desirable solution in such an environment. Due to the number of time constraints, it is more convenient to get a personalised itinerary of activities rather than a list of top-n. In this paper, we present a user study conducted in order to create a preliminary dataset that simulates users' attendance of a cruise and sheds the light on the activity selection behaviour. We discuss challenges faced by the itinerary recommendation and illustrate them with user study examples.