The coronavirus disease 2019 (COVID-19) pandemic has had a huge effect on adolescents' health and learning. Health promotion strategies should be valued, and life skill education is a potential approach in this direction. This study aimed to investigate the implementation of an evidence-based life skill education programme during the COVID-19 pandemic in the Lombardy Region (Italy) by collecting opinions about the programme's usefulness and feasibility and identifying the strategies for implementing it through distance teaching. The study involved 63 middle school expert teachers, principals or coordinators in life skill education. An online questionnaire with closed- and open-ended questions was used. A qualitative content analysis was carried out using N-Vivo Answers software. The participants recognized the high value of life skill education at the time of COVID-19, but they showed reticence regarding its feasibility. Positive effects of the programme on both health and learning outcomes were reported. The obstacles were related to interpersonal aspects, student involvement, methods, organization and planning. Many strategies were suggested related to the teaching method, the curriculum organization and the adaptation needs. These strategies can be used to implement active and cooperative learning at a distance to reinforce students' life skills to cope with the crisis and promote their health.