This paper aims at presenting a set of travellers’ typologies using attributes characterizing people’s attitude, through an Exploratory Factor Analysis (EFA), and a subsequent cluster analysis (CA), based on the obtained latent constructs. The final goal is to contribute to deepen the knowledge on market segmentation in order to define more people-oriented transport policies, focusing on a medium size Italian city, Alessandria. Six factors have been defined on which the k-means cluster analysis has been applied finding four travellers’ profiles.Results confirm certain hypothesis from behavioural psychological theories. Attitude–behaviour relationships loosen when habits, consolidated in time, do intervene; moreover in small-medium urban context, as opposed to large and dense cities, insufficient transport supply does not favour the use of alternative modes to the motor vehicle, if not to the cost of a great loss in efficiency. In fact, the study shows how significant constraints such as necessity, time saving, and low transport supply (mainly designed around students going to school) are in determining a behavioural change, so that the “right general attitudes” are not sufficient to obtain a real modal shift. This leads to expect opportunistic behaviours, even within a overall positive attitude towards the environment. Actually, that overall positive attitude is not enough to prompt consistent behaviour unless a marked self-control and strong motivation are present. These two features seem to be missing in the interviewed sample of population, unlike what emerges from other studies undertaken in Northern Europe. The geographic location most likely plays a significant role in such a difference. Indeed, cultural background and the prevailing habits of the population may well explain the “slackening” of the bond between moral norms and behaviour, and the subsequent search for surrogates (e.g. the high willingness to pay for environmental protection) to justify the unwillingness to forgo the private vehicle on behalf of more sustainable modes.Finally, our study seems to prove that education could play a key role in transport policy formulation but, moreover, in social policy, as individuals more akin to modal shift are those showing higher levels of instruction.