Migration worldwide is characterized by the presence of unaccompanied minors, separated from their parents or any primary caregivers. The present study aimed to fill literature gaps on the acculturation and adaptation of unaccompanied migrant and refugee adolescents. The Ward and Geeraert model (2016), which explores how acculturation unfolds within different ecological contexts, namely societal, institutional and familial, was employed to understand which aspects of the youths’ reality in the host country can facilitate or challenge their psychological and sociocultural adaptation. Since education is vital for the psychosocial and economic adjustment of migrant adolescents, this research focused on the various learning settings of unaccompanied youths, including schools, residential communities, and initiatives offered by NGOs. Semi-structured interviews were conducted with nine adolescents and eleven stakeholders in Italy, one of the European countries hosting the highest number of unaccompanied minors. Language barriers and perceived discrimination were described as potentially challenging the youths’ psychological adaptation, further complicated by their transition to adulthood. Normative developmental changes seemed to add weight to acculturative stressors and the termination of the protection system at eighteen meant that these adolescents had to abandon academic and career ambitions to become self-sufficient. Educational settings provided youths with competence in both majority and ethnic cultures, thus potentially favouring their sociocultural adaptation. However, the difficult access to mainstream Italian schools deprived them of a significant channel to integration, which was promoted by alternative measures that could be internationally employed, such as the “Apartments for Autonomy” and voluntary guardianship.