The conservation of historical urban centres is an important resource to encourage liveability and sustainable development of cities in the context of global climate change. It is a complex process that serves diverse perspectives, among them is the thermal comfort. The paper analyze the contribution of street configuration towards the improvement of thermal comfort at pedestrian level, in the Old Town of Camagüey-Cuba (World Heritage Site, since 2008). Simulations performed are run for summer and winter solstices by using RayMan model. The urban settings are represented by symmetrical street canyons (380 m long, 9 m width), with different solar orientations (i.e. N–S, NE–SW, E–W, NW–SE) and aspect ratios (i.e. H/W = 0.5, 1, 1.5, 2, 3, 4, 5). Results are presented in terms of Physiologically Equivalent Temperature (PET). Our findings confirm that the spatial distribution of thermal conditions at street level, depend strongly on aspect ratio and street orientation. The results show extreme patterns of thermal comfort between N–S and E–W streets. Rotation to N–S orientation is a valid strategy to mitigate the heat stress in summer, with reductions of up to 2 h at the center of the street. Aspect ratios between 1 and 1.5 offer a quite acceptable thermal performance for summer and winter. PET patterns discussed give information about the most suitable locations for pedestrian within the street. The urban guidelines presented enable to urban planners rehabilitate and design cities, which are able to reduce the impact of thermal stress in hot-humid climates. The results could be included in the Urban Regulations of Camagüey. •Liveability and sustainable development of urban centres in the context of global climate change.•The contribution of street configuration towards the improvement of human thermal comfort conditions.•Support to evaluate temporal-spatial distribution of extreme thermal conditions at pedestrian level.•Suitable spaces, uses of the street, and bioclimatic resources of design into urban canyons.•Urban guidelines to design cities, which are able to reduce the impact of thermal stress.