According to the literature, the path choice decision process of a user of a (road) transport network, named path choice problem (PCP), is composed of two levels/models: the definition of perceived alternative paths (choice set) and the choice of one path in the path choice set. The path choice probability can be estimated with two models: a choice model of the path choice set and a choice model of a path (Mansky paradigm). In this research, the paper’s contribution concerns two elements: extension of the PCP paradigm (two-level models) consolidated in the literature to the route choice decision process (vehicle routing problem (VRP)) and identification of common elements in the PCP and VRP concerning the criteria in the two decision levels and the procedure for route and path selection and choice. The experiment concerns the comparison of observed routes with simulated and optimized routes of commercial vehicles to analyse the level of similarity and coverage. The observed routes are extracted from floating car data (FCD) from commercial vehicles travelling inside a study area inside the Calabria Region (Southern Italy). The comparison is executed in terms of similarity of the sequences of nodes visited between observed routes and simulated/optimized routes.