This paper analyses the prevailing entrepreneurial profiles within Italy’s professional agricultural sector, using data from the 7th Italian National Institute of Statistics (ISTAT) Agricultural Census, 2020. Access to micro-data from the complete spectrum of Italian farms allowed us to perform to an extensive analysis of the entrepreneurial profiles. Moving from market-oriented farms with stable market relationships and a minimum threshold of economic production, we identified nine distinct profiles by using hierarchical cluster analysis and a set of structural and managerial indicators supported by the current literature. These profiles vary significantly in terms of the age of farmers, the economic size of farms, the type of farming, human capital, and strategic orientation. The age of farmers is a particularly powerful variable to discriminate among the entrepreneurial profiles. Although young farmers are often more innovative than older ones, the spectrum of entrepreneurship is wide and diverse, especially regarding the diversification of activities. Our results confirm a complex picture of farm management in Italy, where corporate businesses integrated into the agro-food system coexist with small farms and part-time farmers. Such representation calls for more targeted public support policies that address specific needs and potential role of different types of farmers.