This paper investigates how much Italian farms are involved in the so-called “Agriculture 4.0” (Agri 4.0) journey. The paper focuses on analyzing the knowledge and adoption levels of specific 4.0-enabling technologies while also considering the main benefits and obstacles. A descriptive survey was carried out on a total of 670 respondents related to agricultural companies of different sizes. The findings from the survey demonstrate that Italian farms are in different positions in their journey toward the Agri 4.0 paradigm, mainly depending on their size in terms of revenues and land size. Furthermore, there are strong differences concerning both the benefits and obstacles related to the adoption of the Agri 4.0 paradigm, here depending on the technology adoption level. Regarding future research, it would be interesting to carry out the same study in other countries to make comparisons and suitable benchmark analyses. Although scholars have debated about the adoption of technologies and the benefits related to the Agri 4.0 paradigm, to the best of the authors’ knowledge, no empirical surveys have been carried out on the adoption level of digital solutions in agriculture in specific countries.