Vitoria-Gasteiz has taken several urban greening actions such as the introduction of a ring of parks that connect the city’s surroundings, a sustainable mobility plan, and urban green structure strategies. Previous studies establish a connection to the importance of greening to mitigate the surface urban heat island (SUHI) and evaluate the effectiveness of these measures on urban climate. In this study, land surface temperature (LST), a remote sensing (RS) parameter, recorded by Landsat satellites (5, 7, and 8) was used to evaluate the effect of SUHI in Vitoria-Gasteiz between 1985–2021. The aim was to evaluate whether the urban greening actions influenced the local thermal conditions and, consequently, helped minimize the SUHI. Thirty sampling locations were identified, corresponding to different local climate zones (LCZ), at which LST data were extracted. A total of 218 images were processed and separated into summer and winter. Four of the 30 locations had, since 2003, on-site meteorological stations with regular air temperature (Tair) measurements which were used to validate the LST data. The results showed that Spearman’s correlation between Tair and LST was higher than 0.88 in all locations. An amount of 21 points maintained the same LCZ classification throughout the analysed period and nine underwent a LCZ transformation. The highest average temperature was identified in the city centre (urbanized area), and the lowest average was in a forest on the outskirts of the city. SUHI was more intense during the summer. A significant increase in SUHI intensity was identified in areas transformed from natural to urban LCZs. However, SUHI during satellite data acquisition periods has shown a minimal change in areas where sustainable practices have been implemented. RS was valuable for analysing the thermal behaviour of the LCZs, despite the limitation inherent in the satellite’s time of passage, in which the SUHI effect is not as evident.