Vehicle Routing Problems (VRP) comprise many variants obtained by adding to the original problem constraints representing diverse system characteristics. Different variants are widely studied in the literature; however, the impact that these constraints have on the structure of the search space associated with the problem is unknown, and so is their influence on the performance of search algorithms used to solve it. This article explores how assignation constraints (such as a limited vehicle capacity) impact VRP by disturbing the network structure defined by the solution space and the local operators in use. This research focuses on Fitness Landscape Analysis for the multiple Traveling Salesman Problem (m-TSP) and Capacitated VRP (CVRP). We propose a new Fitness Landscape Analysis measure that provides valuable information to characterize the fitness landscape’s structure under specific scenarios and obtain several relationships between the fitness landscape’s structure and the algorithmic performance.