Lisbon is a European Mediterranean city, greatly exposed to heatwaves (HW), according to recent trends and climate change prospects. Considering the Atlantic influence, air temperature observations from Lisbon’s mesoscale network are used to investigate the interactions between background weather and the urban thermal signal (UTS) in summer. Days are classified according to the prevailing regional wind direction, and hourly UTS is compared between HW and non-HW conditions. Northern-wind days predominate, revealing greater maximum air temperatures (up to 40 °C) and greater thermal amplitudes (approximately 10 °C), and account for 37 out of 49 HW days; southern-wind days have milder temperatures, and no HWs occur. Results show that the wind direction groups are significantly different. While southern-wind days have minor UTS variations, northern-wind days have a consistent UTS daily cycle: a diurnal urban cooling island (UCI) (often lower than –1.0 °C), a late afternoon peak urban heat island (UHI) (occasionally surpassing 4.0 °C), and a stable nocturnal UHI (1.5 °C median intensity). UHI/UCI intensities are not significantly different between HW and non-HW conditions, although the synoptic influence is noted. Results indicate that, in Lisbon, the UHI intensity does not increase during HW events, although it is significantly affected by wind. As such, local climate change adaptation strategies must be based on scenarios that account for the synergies between potential changes in regional air temperature and wind.