The fight against alien invasive insect pests of plants in the urban environment often affects varied sectors of the economy, landscape gardening, public health, and ecology. This paper focuses on the evolution of the red palm weevil in San Benedetto del Tronto, a coastal urban area in central Italy. We investigated the evolution of this insect pest of palm trees in the 2013–2020 period, considering both the effectiveness of the chemicals used and their potentially harmful effects. With a multidisciplinary approach, we carried out a spatio-temporal analysis of the extent and mode of pest spread over time using historical aerial photos, freely available remote sensing images, and field surveys integrated in a GIS environment. We also assessed the toxicity risk associated with the chemicals used to protect the palms from the red weevil. The fight against this weevil is now concentrated in specific areas such as parks, roads, villas, hotels, farmhouses, and nurseries. The preventive chemical treatments applied are very effective in preserving the palms, but they show a toxic potential for all organisms. We discuss current local management of this pest, focusing on several aspects involved in the fight against this beetle in an urban area.