The adoption of Industry 4.0 technologies has become particularly important nowadays for companies in order to optimize their production processes and organizational structures. However, companies sometimes find it difficult to develop a strategic plan that innovates their current business model and develops an Industry 4.0 vision. To overcome the growing uncertainty and dissatisfaction in implementing Industry 4.0, new methods and tools that specifically address dedicated companies’ areas, such as logistics, supply chain management, and manufacturing processes, were developed to provide guidance and support to align companies’ business strategies and operations. In particular, this paper develops and presents the application of a maturity model for Logistics 4.0, focusing on the specific applications of Industry 4.0 in the area of logistics. To do so, extant maturity models, linked to the context of Industry 4.0 implementation in logistics processes, were examined in the main scientific research. Afterward, two companies have been investigated through a survey, built around three fundamental macro-aspects, named (i) the propensity of the company towards Industry 4.0 and Logistics 4.0, (ii) the current use of technologies in the logistics process, and (iii) the investments’ level towards Industry 4.0 technologies for a Logistics 4.0 transition. By doing so, a maturity model for Logistics 4.0 emerged as the main result of our research, able to identify the level of maturity of companies in implementing the Industry 4.0 technologies in their logistics processes. Moreover, the model highlighted the strengths and weaknesses of the two investigated companies with respect to the transition towards Logistics 4.0. On the basis of the obtained results, a roadmap for enhancing the digitalization of logistics processes, according to the principles of the fourth industrial revolution, was finally proposed.