The impact of freight transport in cities is significant, and as such correct planning and management thereof help reduce their enormous negative impact. Above all, the special large vehicles have a greater impact than the remainder of freight vehicles, so a special attention should be paid to them. The vehicles which supply or pick up large amounts of goods at specific points throughout the city are an example of this type of vehicles. The aim of this paper is to minimize the cost of this freight transport type from a social, economic, and environmental viewpoint. To this effect, an optimization model has been proposed based on bilevel mathematical programming which minimizes the total system costs. City network model data are obtained on the lower level such as vehicle flow and travelling times, which are then used on the upper level to calculate total system costs. The model has been applied to a real case in Santander (Spain), whose final result shows the size and typology of the fleet of vehicles necessary to have the least impact on the city. The greater the vehicles size is (i.e., using fewer trucks), the less the cost of the freight transport is.