The smart and resilient city evolves by slow procedures of mutation without radical changes, increasing the livability of its territory. The value of the city center in a Smart City can increase through urban lighting systems: its elements on the territory can collect and convey data to increase services to city users; the electrical system becomes the so-called Smart Grid. This paper presents a study of smart lighting for a small town, a touristic location inside a nature reserve on the Italian coast. Three different approaches have been proposed, from minimal to more invasive interventions, and their effect on the territory has been investigated. Based on street typology and its surroundings, the work analyzes the opportunity to introduce smart and useful services for the citizens starting from a retrofitting intervention. Smart city capabilities are examined, showing how it is possible to provide new services to the cities through ICT (Information and Communication Technology) without deep changes and simplifying the control of basic city functions. The results evidence an important impact on annual energy costs, suggesting smart grid planning not only for metropolis applications, but also in smaller towns, such as the examined one.