Factors influencing walking mobility are shaped by a range of urban conditions, including infrastructure, individual attitudes, and urban-planning strategies. Although Italy has begun to promote walking mobility, many challenges remain—for instance, safety during travel, the environmental quality of public space, and the accessibility of destinations. This study aims to contribute to this debate by analysing the main dynamics identified in the literature in the Italian context: (1) environmental and infrastructural correlations (e.g., air quality, availability of green space, accessibility); (2) resilience to external factors (e.g., heat waves, road safety); and (3) socio-economic and behavioural dimensions (e.g., income, car use, purpose of travel). The paper draws on a national dataset covering 106 Italian cities across metropolitan and non-metropolitan contexts, combining data from ISTAT, ISPRA, and the ‘BES’ indicators to examine the effects of environmental factors such as air quality, safety levels during trips, and transport infrastructure. The methodology is structured in three parts: the study estimates the relationships between these factors and walking mobility using an econometric model; then it examines how the relevant factors vary across Italy’s regions. The results provide timely guidance for urban-mobility planning, underscoring the need to prioritise the safety of vulnerable users and to improve urban accessibility. Overall, the study highlights the value of embedding active mobility within integrated urban strategies to create healthier, more accessible, and more liveable cities.