The study analyzes and explains on-farm diversification in Emilia-Romagna, a productive and agriculturally intensified region in Italy. The purpose was to contribute to knowledge gaps on the adoption of different diversification strategies in relation to farming system. Based on farm-level census data gathered by the Italian National Institute of Statistics during the sixth general agricultural census, two on-farm diversification pathways were investigated: deepening and broadening. The farmer’s decision to diversify activities and the identification of diversification pathways were analyzed using logit and multinomial logit models. The results show that arable farms adopt broadening strategies, intensive farms opt for deepening ones, and specialized adopters of quality schemes combine both strategies. Furthermore, in contrast to the existing research, the study highlights that intensive farms are more likely than arable farms to diversify. Finally, the findings provide insights to improve analyses in the context of policy and regional strategic support.