Young, skilled and educated Italians have been emigrating in record numbers: About 160,000 Italians moved abroad in 2018 alone. While much of recent research focused on the economic drivers of this spatial mobility, this article explores highly skilled Italians’ mobile life projects from a gender perspective. Our study was guided by the following research questions: How do mobility and migration intersect with gender relations and career success in the lives of highly skilled Italians living abroad? What role does gender play in highly skilled Italians’ decisions about moving and staying abroad? Our research, which drew on semistructured in-depth interviews conducted with 51 university graduates, was part of a larger study of the determinants and trends in the new migration of the highly skilled from Tuscany, a region in Italy. Using Strauss and Corbin’s three-stage coding process to analyze the interviews, we identified four core themes of particular concern to participants when comparing Italy with the contexts they encountered abroad: gender-sensitive culture in the workplace, strategic and dialogic mobile life projects, impact of state and workplace policies and (subjective) age vis-à-vis temporariness. Our results both confirmed the findings of previous studies and prompted new questions in need of further investigation, such as experiences of gender (in)equality and their power to transform short-term mobility into mobile life projects or permanent migration, dual-career couples’ spatial mobility, and the impact of mobility on normative beliefs about key life events.