The lack of understanding and definitional inconsistencies regarding agritourism and the importance of cooperation in sustaining this kind of tourism are underlined in the literature. This study analyzes the perceptions of agritourism and cooperation from actors in the sector using a plurality of methods, including unsupervised (a) text mining and (b) sentiment analysis with the use of a lexical database, as well as (c) supervised qualitative data analysis. Based on the assumption that destinations with different geographic characteristics have different features and products, two different destinations as for its accessibility and tourism recognition were selected for comparison: (a) an island—Lesvos in the North Aegean Sea, and (b) a continental mountain region—Plastiras Lake, in Greece. The data were collected from personal in-depth interviews and with the use of semi-structured questionnaires. From a methodological perspective, all three methods provided unique insights on the study’s themes, and the overall image of agritourism and cooperation was positive. A common understanding seems important for cooperation and networking; however, training is needed not only for effective promotion of agritourism, but also for cooperation techniques, benefits, trust-building mechanisms and best practices.