Adolescence is a phase in which many challenges and changes occur in the lives of youth and their families (Buist, Deković, Meeus, & van Aken, 2004). One of the most important changes concern relationships and its members. The main aim of this study was to explore the perception of attached relationships to mother, father and peers in a community sample of early and mid-adolescents. For this purpose, the Inventory of Parental and Peer Attachment (IPPA revised form; Armsden & Greenberg, 2009) was administered to 2000 Italian adolescents. Age and gender-related differences were considered. The results of the present study suggested that Italian adolescents continue to perceive the attachment relationships to parents as secure and trustable. The data showed a general decreasing trend of attachment security from early to mid-adolescence which apply for maternal, paternal and peer relationships. Moreover, gender differences have emerged for paternal and peer attachment relationships, with boys reporting higher levels of attachment to father and lower levels of attachment to peers, than girls. Possible explanations and implications were discussed.