Cycling for transportation is increasingly recognised as a core strategy to combat the climate emergency, particularly in urban environments. Within this context, bike-sharing systems offer a valuable opportunity to attract new users to cycling and promote sustainable mobility. However, the rapid growth in the use of these schemes has exposed critical gaps—such as insufficient cycling infrastructure, system saturation, and poor integration with other transport modes—which continue to hinder their full potential. Drawing on a mobile methodology, which allowed participants to reflect in situ on their perceptions, reactions, and decision-making processes as they unfolded, we conducted video-recorded bike-along interviews with 17 users of a docked bike-sharing system in Barcelona to explore how infrastructural and spatial conditions shape the riding experience. Through a combination of content analysis of participants’ narratives and observational analysis of videotaped behaviours, which captured behavioural cues, bodily gestures, and micro-negotiations with traffic and infrastructure that were often left implicit in verbal accounts, our findings reveal that traffic safety—modulated by cycling infrastructure and network connectivity—strongly influences how users of shared bicycles perceive and engage with urban space. Furthermore, participants reported that features specific to shared bicycles, including their design and maintenance, notably shaped their riding experience. Beyond the act of cycling itself, our analysis highlights the importance of often-overlooked stages—such as bike pick-up and return processes—in shaping users’ overall perceptions. These moments present logistical and accessibility challenges that may limit the consolidation and expansion of bike-sharing schemes. Policymakers and urban designers are likely to find these insights valuable, as they point to concrete areas for improvement that could enhance navigation, usability, and user satisfaction.