In the present work, the effects of surface chemistry and micro/nanostructuring on the Leidenfrost temperature are experimentally investigated. The functional surfaces were fabricated on a 304 stainless steel surface via femtosecond laser surface processing (FLSP). The droplet lifetime experimental method was employed to determine the Leidenfrost temperature for both machine-polished and textured surfaces. A precision dropper was used to control the droplet size to 4.2 μL and surface temperatures were measured by means of an embedded thermocouple. Extraordinary shifts in the Leidenfrost temperatures, as high as 175 °C relative to the polished surface, were observed with the laser-processed surfaces. These extraordinary shifts were attributed to nanoporosity, reduction in contact angle, intermittent liquid/solid contacts, and capillary wicking actions resulting from the presence of self-assembled nanoparticles formed on the surfaces. In addition to the shift in the Leidenfrost temperature, significant enhancement of the heat transfer in the film boiling regime was also observed for the laser-processed surfaces; water droplet evaporation times were reduced by up to 33% for a surface temperature of 500 °C.