The concept of Industry 5.0 is novel from many points of view, as it fosters the transition to a sustainable, human-centric, resilient European industry. To reach this ambitious goal, it is necessary to act simultaneously on many fronts, starting from guaranteeing basic human rights (e.g., privacy, independence, and dignity) and paying attention to the circular economy and energy efficiency. Despite being difficult to adopt in its general formulation, this concept can be scaled up to specific fields, thus producing increased value with repercussions to the whole industrial process. The winemaking industry puts Italy at the forefront globally, as it is also among the key components of the whole national agrifood/agritech value chain. However, the Italian winemaking industry is quite fragmented, with a heterogeneous mix of small and medium enterprises (SMEs) and with large companies having opposite approaches to the production process, both in terms of involvement of human resources and seasonality of efforts, due to the existing climate differences nationwide. This fact makes the adoption of common practices even harder but makes the benefits of projects promoting this process innovation more tangible. In such a framework, CANTINA 5.0 seeks to fill in this important gap, promoting the Industry 5.0 principles in a selected group of SMEs and large companies from two different Italian areas featuring different climate conditions and different seasonality, hence characterized by different wine harvesting periods and types of wine production. The present article deals with the description of this paradigm in its single parts, including the use of questionnaires and smart tools to detect the health and well-being state of factory workers and winemakers, the use of well-grounded (including gas chromatography/mass spectrometry) and novel (e.g., based on the Internet-of-Things) environmental monitoring tools applied to the cellars/production departments, and the sensory analysis of the end-products, also leveraging the chemical and emotional characteristics of wines produced using the Industry 5.0 approach.