COVID-19 has shaped and changed our normalities, and, with the discovery of new variants, the long-COVID syndrome, and stress disorders, the end of the pandemic seems distant. The current scenario is impacting all aspects of our lives. In particular, many studies reported that the pandemic resulted in increased psychiatric disorders and grief-related symptoms in adolescents. The project developed between Italy and Slovenia investigated students’ experiences during the lockdown and, in particular, reported the perception of distanced learning, producing a transparent qualitative analysis that can inform future research and open to discussions on learning strategies. A survey was conducted with secondary school students in Southern Italy between 1 April and 31 May 2020 and in Central Slovenia between 16 March and 28 February 2021. Qualitative and quantitative data were collected based on students’ perception of distanced learning, via an online survey platform. The results focused on three main aspects: learning experience, relationships with peers and teachers, and anxiety levels. The data showed similarities and differences in the two cohorts and suggested strategies to improve education (e.g., with blended approaches) to prepare students, teachers, and tutors for the challenges of returning to classes. In particular, data showed that it is recommended to foster collaboration between EU countries and to work to prevent students’ social isolation.