Aimed at climate-responsive urban design for tropical areas, the paper attempts to answer the question whether the site-related context affects in some way the perceptual assessment of the microclimate by users of outdoor spaces. Our hypothesis was that visual cues resulting from urban design are important components of the outdoor thermal perception. Monitoring was carried out alongside the administration of standard comfort questionnaires throughout summer periods in 2012-2015 in pedestrian areas of downtown Rio de Janeiro (22° 54 10 S, 43° 12 27 W), Brazil. Campaigns took place at different points, pre-defined in respect of urban geometry attributes. For the measurements, a Davis Vantage Pro2 weather station was employed to which a gray globe thermometer was attached. Two thermal indices were used for assessing the overall meteorological conditions and comfort levels in the outdoor locations: physiological equivalent temperature (PET) and universal thermal climate index (UTCI). Our results suggest that thermal sensation in Rio depends to a large extent on the thermal environment as described by air temperature, PET, or UTCI, and that urban geometry (expressed by the sky-view factor (SVF)) may modify this relationship with increased building density associated to warmer sensation votes under moderate heat stress conditions. This relationship however reverses under strong heat stress with warmer sensations in less obstructed locations, and disappears completely under still higher heat stress, where meteorological conditions, and not the site's SVF, will drive thermal sensation.