This article presents the data collected through an extensive research work conducted in a historic hilly town in central Italy during the period 2016-2017. Data concern two different datasets: long-term hygrothermal histories collected in two specific positions of the town object of the research, and three environmental transects collected following on foot the same designed path at three different time of the same day, i.e. during a heat wave event in summer. The short-term monitoring campaign is carried out by means of an innovative wearable weather station specifically developed by the authors and settled upon a bike helmet. Data provided within the short-term monitoring campaign are analysed by computing the apparent temperature, a direct indicator of human thermal comfort in the outdoors. All provided environmental data are geo-referenced. These data are used in order to examine the intra-urban microclimate variability. Outcomes from both long- and short-term monitoring campaigns allow to confirm the existing correlation between the urban forms and functionalities and the corresponding local microclimate conditions, also generated by anthropogenic actions. In detail, higher fractions of built surfaces are associated to generally higher temperatures as emerges by comparing the two long-term air temperature data series, i.e. temperature collected at point 1 is higher than temperature collated at point 2 for the 75% of the monitored period with an average of +2.8 °C. Furthermore, gathered environmental transects demonstrate the high variability of the main environmental parameters below the Urban Canopy. Diversification of the urban thermal behaviour leads to a computed apparent temperature range in between 33.2 °C and 46.7 °C at 2 p.m. along the monitoring path. Reuse of these data may be helpful for further investigating interesting correlations among urban configuration, anthropogenic actions and microclimate variables affecting outdoor comfort. Additionally, the proposed dataset may be compared to other similar datasets collected in other urban contexts around the world. Finally, it can be compared to other monitoring methodologies such as weather stations and satellite measurements available in the location at the same time.