The paper presents the results of shading analysis which was carried out as part of a wider comparative analysis of two sites with different characteristics in terms of street geometry and urban density. The first experiment site was a traditional settlement in the island of Tinos, Greece, and the second was a relatively newly built part of the capital city of the island. Also a parametric shading analysis was carried out in order to examine a number of parameters that influence shading conditions in urban canyons. The paper aims in analyzing the effect of parameters such as urban layout, street geometry and orientation on solar access and shading conditions, which strongly affect urban canyon microclimate. The results of shading simulations are compared to the results of experimental measurements of air and surface temperatures and to parametric thermal analysis results. The conclusions can contribute in the formulation of urban design guidelines. (C) 2013 Elsevier Ltd. All rights reserved.