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The analysis of tandem truck–drone delivery systems has recently attracted the attention of the research community, mainly focused on extending classical operational research problems such as the multiple traveling salesperson or the vehicle-routing problem. In this paper, we explore the design of an urban massive combined delivery system using a continuum approximation (CA) method for a circular city characterized by a certain density of customers. Starting from a set of parameters defining the main characteristics of trucks and drones, a sectorization of the delivery area is first determined. Then, for a given truck capacity, the optimal number of trucks is obtained considering different scenarios using three integer programming models. We propose several performance indicators to compare the tandem approach with the alternative solely truck delivery system.