Walking reports numerous benefits for older persons, yet its practice can be hindered by the built environment. This article seeks to understand how and why certain elements of the built environment facilitate or impede the everyday trips older persons complete on foot. It reports the findings of a set of walking interviews conducted in four central neighbourhoods of Santiago de Chile, where forty older persons were invited to walk and talk about the trips they complete on foot and the aspects that facilitate or hinder them. The findings reveal that older persons are aware of the benefits of walking and travel regularly on foot despite the barriers they find in their neighbourhoods. The presence/absence of greenery, the conditions of the facades and the level of cleanliness of the streets affect older persons’ walking experience and can increase/diminish their willingness to walk. Damaged and poorly designed pedestrian infrastructure can cause fear, provoke accidents and become serious hazards. Older persons develop strategies to overcome these barriers, yet the data suggest that they see Santiago as a “disabling city” because it has obstacles that could be unsurmountable in a near future if an illness or an accident diminishes their abilities.