This work explores the concepts of work readiness and self-perceived employability, addressing contextually the perceptions from third-year bachelor students enrolled in the degree of Cultural Heritage and Tourism at the University of Macerata in academic year 2018-2019. The research aim was to identify perceptions of undergraduates in terms of skills and employability potential to design effective teaching interventions. Following literature review, the paper describes collected data and discusses around key research questions, related to (a) perception the world of work; (b) assessment of possessed skills; (c) estimation of employment possibilities; (d) perception of preparation to the labour market. Results show a gap between perceptions of the labour market and possessed skills, a medium-low self-perceived employability, and a low engagement in career development activities, where, to the other hand, perceived preparation provided by the university is declared as medium-high. Conclusions highlight the need of further work to better understand the implications of results for effective learning design.