The issue of place attachment and mobility was frequently studied with reference to university students moving away from their home country. This situation may provide interesting opportunities for a personal growth, but can also be a source of adaptation difficulties, thus leading to psychological troubles, and making people desire to go back to their home country. That’s what is defined homesickness. Homesickness probably plays a role in the relationship between the old and the new place of residence, thus influencing multiple place attachment. The literature on this topic did not clearly show how a strong affective bond with the home country can influence the psychological attachment to a new place. With reference to students, some studies showed the negative influence of homesickness on the development of a psychological attachment with a new place of residence. Our study was aimed at exploring the psychological processes influencing the relationship between the old and the new residential setting in students after transition to university. We also considered the role of personality, situational and environmental variables (distance between the two places and size of the new place) in the development of homesickness. Students from two Italian university cities participated in the study. We developed a questionnaire measuring the following variables: place attachment to the home country and to the new place of residence; susceptibility to homesickness and actual homesickness; socio-demographic and residential experience variables. Factor analyses showed the existence of different dimensions in the affective bond with the home country, referring to personal identity, practical resources, and social relationships; a general dimension of attachment to the new place of residence; and three personality dimensions referring to the need of social support, rigidity and coping difficulties. A regression analysis showed that students having stronger social relationships in their home country and a lower level of place attachment with the university city suffer from feelings of homesickness. Both personality factors and environmental/situational variables showed a significant impact on the effective presence of homesickness. Finally, students who have suffered from homesickness earlier in life experienced stronger difficulties in the adaptation process to the new residential situation. Implications for the study of place attachment will be discussed.