It is well known by now the sensitiveness of the scholastic world towards pupils whom, for health reasons, cannot regularly attend the everyday classroom lectures. This is attested from regulations of Hospital Schools and, more recently, from the so-called Homebound Education (HE).

Although it is perceived as a poor substitute for real school by students themselves, HE grants the academic instruction (Bessel, 2001; Searle, 2006). Students in HE often report feelings of isolation and loneliness (A’Bear, 2014; Arora, 2006; Bessell, 2001; Suzuki and Kato, 2003), exacerbated by the impossibility to attend school trips and extracurricular activities (Lomabaert et al., 2006).
In Italy, specific administrative procedures must be respected to have access to HE services.

The homebound education can perform in three different contexts:
• the children or young people will receive homebound education in their own homes;
• the children or young people will receive the homebound education in other residential communities;
• the children or young people will receive homebound education at the hospital where it isn’t present a school service.

In the latter two cases, HE students will relate with unknown teacher, while in the first case the homebound teachers are students’ classroom teachers. When HE is performed in residential communities or in hospital, teachers provide direct instructions to HE students, even though the responsibility for the long-term planning of students’ educational programs remains to classroom teachers, in collaboration with HE teachers and school team.

In this context of homebound education great expectations are coming out about the possibility of using technologies (mainly those of Web 2.0) to empower teaching/learning processes at home, usually based on few hours of physical presence of a teacher at the young inpatient’s domicile.

In fact, it doesn’t involves however just the use of videoconference as a tool for replacing participation at distance lessons, but rather the realization of personalized labs for learning (Personal Learning Environments, usable at home, build for the young inpatient by teachers and animated from various actors (classmates, teachers, parents, friends).

Considering the growing interest in involving Web 2.0 technologies in HE, the present study aims to investigate how Italian teachers manage a HE process, which learning strategies they employ, and which technologies they use to promote an inclusive teaching, both academically and socially. Moreover, we investigate the factors, which can impede the integration of technologies in teaching activities.
1280 Italian teachers completed an online questionnaire, investigating the abovementioned issues. Results highlight that teachers are not keen to integrate technologies in their teaching strategies, both for the organization and performance of their activities, even in the specific case of HE where an integrated use of technologies could be helpful. Our results show that this lack of integration could be addressed to several teachers’ personal factor (i.e, older age, their discipline, and school level of teaching).