A substantial proportion of Italian students are unaware of the connection between what they learn at school and their work opportunities .This proportion would most likely increase if data were collected today, given the generation of a broad range of new jobs that has arisen due to advancements in technology. This gap between students’ understanding of what they learn at school and its application to the broader world—the society, the economy and the political sphere—suggests there needs to be a rethinking of how teaching and learning at school is conceived and positioned. To help students to approach ongoing social and economic transformations, the Italian Educational Ministry (MIUR) has endorsed a school–work interchange program which, aligned with the principle of open schools, aims to provide students with work experience. It is within the scope of this initiative that we have tested high school students with remote sensing (RS) from space projects. The experience-based approach aimed to verify students’ openness to the use of satellite data as a means to learn new interdisciplinary skills, to familiarize themselves with methodological knowledge and, finally, to inspire them when choosing a university or areas of future work. We engaged three cohorts, from 2017, 2018 and 2019, for a total of 40 h each year, including contact and non-contact time. The framework of each project was the same for the three cohorts and focused on the observation of Earth from space with a specific focus on wildfires. However, the initiative went beyond this, with diverse activities and tasks being assigned. This paper reports the pedagogical methods utilized with the three cohorts and how these methods were transformed and adapted in order to improve and enhance the learning outcomes. It also explores the outcomes for the students, teachers and family members, with respect to their learning and general appreciation.