This study investigates the impact of digital technologies on the logistics sector, focusing on last-mile delivery in the food delivery industry in Italy. The research specifically compares two cities, Urbino and Milan, highlighting the differences in how Just Eat and Glovo operate in urban and peripheral contexts. In Urbino, small restaurant businesses face significant logistical challenges due to the absence of a robust food delivery network, requiring them to handle delivery services independently. This contrasts with Milan, where both platforms offer more comprehensive delivery solutions. By analyzing variables such as delivery price, minimum order price, delivery times, and customer reviews, the study identifies Glovo’s flexible business model as better suited to smaller cities like Urbino, where fluctuating demand and limited resources make managing logistics difficult. The case of Alfonsino, a food delivery platform that has successfully operated in small towns, further supports this conclusion. The findings suggest that adopting a model like Glovo’s “Order & Delivery,” which offers greater flexibility and lower costs, could enhance delivery services in smaller cities. The research also highlights future opportunities for exploring the environmental impacts of crowdshipping and the role of technological advancements, such as autonomous delivery, in shaping the future of last-mile logistics.