In this paper, we present a work-flow to investigate the joint visibility between very-high-resolution SAR and optical images of urban scenes. For this task, we extend the simulation framework SimGeoI to enable a simulation of individual pixels rather than complete images. Using the extended SimGeoI simulator, we carry out a case study using a TerraSAR-X staring spotlight image and a Worldview-2 panchromatic image acquired over the city of Munich, Germany. The results of this study indicate that about 55 % of the scene are visible in both images and are thus suitable for matching and data fusion endeavours, while about 25 % of the scene are affected by either radar shadow or optical occlusion. Taking the image acquisition parameters into account, our findings can provide support regarding the definition of upper bounds for image fusion tasks, as well as help to improve acquisition planning with respect to different application goals.