Thermal stress due to high temperatures has different negative effects on citizens as it generates a decrease in physical capacity and causes cardiovascular and respiratory alterations, which is especially true for pedestrians. In this paper, using a drone, routes for pedestrians with the best thermal comfort were traced between the different headquarters of the Simón Bolívar University (Barranquilla, Colombia). Maps were created for three time intervals, from 10 a.m. to 1 p.m., from 1 to 2 p.m. and from 2 to 3 p.m., and variations in temperature and relative humidity of both natural and artificial shadow areas were identified. The routes with the best thermal comfort were those with natural shade that presented ca. 3 °C less than the unshaded areas. The predominant trees’ genera in most of the traced pedestrian routes were Arecaceae (palm), Tabebuia (purple oak), Mangifera (mango), and Delonix (red acacia). Some of them lose their leaves between March and June, which gives rise to an increase in the temperature along those routes. The developed cell phone application allows for the selection of walking environments with the best thermal comfort, favoring the mobility of the pedestrians along the considered area.