This study addresses the issue of the relationship between place-identity and regional belongingness, which is here developed in liaison with the theme of insularity. Starting from Tajfel’s, Turner’s, Proshansky’s and Moles’s theories, this relationship is further explored, taken into consideration both the construction of personal and social identity, and the attachment bond. The place-identity is a substructure of the personal identity of the individual, which consists of cognitions (ideas, memories, feelings, attitudes, values, meanings, experiences and behavioural tendencies) about the physical world within which they live. At the core of these cognitions is found the environmental past of the individual, which refers to those places which have had a role in the satisfaction or dissatisfaction of their biological, psychological, social and cultural needs (Proshansky, Fabian, Kaminoff, 1983). The place-identity has the “cognitive background function” which allows the recognition of what people see, think and feel, in every situation they interact with the environment (Bonnes, Secchiaroli, 1992). The physical places that have more impact upon the development of the individual’s place-identity, are those characterised by a major novelty and relevance (given the prolonged exposition to them) in the individual’s socialisation pattern and those in which social roles and environmental abilities are learnt. The place-identity is linked to the individual’s well-being and allows them to employ their environmental past as a comparative dimension within new settings (recognition function); to have a picture of its new possible uses (meaning function); to research the congruence between physical contexts and personal identity; to verify the adequacy of the individual’s primary and subordinated aims, in respect of the biological and social human necessities (expressive-requirement function). Essentially, the place-identity is placed in an intersection in which Tajfel’s and Turner’s (1986) social identity and self-identity converge. According to these researchers, the identity feeling is strongly affected, on the one hand, from the awareness of belonging to certain social groups, and, on the other hand, from the specificity of one’s personal story and personality which render one unique. Moles (1985) proposes a taxonomy of islands, on the basis of some variables such as the extension and the generalised distance. In respect of the first aspect, an excessive dimension may turn up for the island in a loss of its insular feature and for its inhabitants in a loss of the perception of the sea boundaries. The generalised distance includes the effective distance from the referent mainland or peninsula, and the material, financial, temporal, cognitive and psychological investment that coming in and going out from an island requires. The combination of these dimensions consents to identifying different degrees of “islandness”, a construct typical of islands, which correspond to as many degrees of insularity as their inhabitants, with unavoidable repercussions on their experiences and life-stories. This ongoing study, started in Italy, but lies within a larger international and cross-cultural research project, aims to explore the role of regional belongingness in the definition of personal identity, taking into account the insular or not insular nature of the referent region. Particularly the topics which this research endeavour to deepen are: 1) whether and when the place-identity coincides with the regional belongingness;2) the perceived influence of one’s own regional belongingness on the life experiences and identities of individuals;3) the valences (emotional-affective, cultural and operative) attributed to this influence; 4) the presence of self-stereotypes referred to the inhabitants of one’s own region;5) the presence of stereotypes and self-stereotypes referred to the characteristics of the inhabitants of an island in comparison with others;6) the spatial dislocation of attachment to places regarding one’s own place of birth;7) the salience of regional boundaries;8) the existence of eventual different answers between insular and non-insular individuals. The data collected were gathered through a semi-structured interview. The sample was composed of four sub-groups, both males and females, and between the ages of 25 and 65. The subgroups were further divided on the basis of their different regional realities, and when coming from an island, on the basis of the different degree of insularity. The primary findings of the first stage of this ongoing project underline the cultural, trans-cultural, and non-cultural factors that make a contribution in the formation of the place-identity.