The paper presents the results of extensive measurements which took place in two sites with different characteristics in terms of street geometry, urban density and materials. The first experiment site was a traditional settlement in the island of Tinos, Greece, while the second was a relatively newly built part of the capital city of Tinos. The experimental measurements, which include air and surface temperature, air humidity and air velocity, were carried out in two sets, during the summer and winter period. The experimental measurements were compared to simulation results obtained by a special computer tool. The comparison led to the conclusion that experimental measurements and program results were in good agreement for the summer period, and the tool was subsequently used in order to perform parametric analysis of microclimate in urban canyons. Main parameters that affect urban canyon microclimate were examined, that is street geometry, street orientation, effect of trees, horizontal surface albedo, wind speed and wind direction. The paper aims in presenting the results obtained by the comparison of the two sites and in analyzing the effect of parameters such as urban layout, street geometry and orientation on urban canyon microclimate, with special reference on the characteristics of traditional architecture of the Cycladic islands. Also, the parametric analysis aims in investigating the parameters involved and their degree of influence on urban canyon microclimate. (C) 2011 Elsevier Ltd. All rights reserved.