A hybrid uniform theory of diffraction (UTD)-physical optics (PO) formulation for the analysis of the multiple diffraction which takes place in urban environments where a cylindrical hill, either smooth or with buildings located on its surface, causes shadowing of the transmitter from the receiver (a non-line-of-sight situation) is presented, thus furthering a previous study published by the authors, in which the hill is modeled as a wedge. The mentioned UTD-PO solution, which is validated by numerical results from technical literature, is of a good computational efficiency, while at the same time increasing the versatility over other methods for the analysis of the same scenarios, since the presented hybrid formulation allows for the study of the above-mentioned environment when the urban area consists of a small number of buildings.