Cyclists belong to the group of vulnerable road users and, thus, need particular protection in road traffic. One way to enhance cyclists’ safety is to use urban data (e.g., infrastructure data, accident statistics) to inform cyclists about potentially dangerous areas, allowing them to better adjust to the situation and elevate their self-protection. However, the question is how to inform cyclists about such dangerous areas. In this paper, we present the results of two field studies, investigating two wearables (headphones vs. smart glasses) and different signal options to inform cyclists about dangerous areas. Study participants were cycling along a predefined track and could experience the different wearables and signals. The main aim of the studies was to find out how cyclists perceive and experience the different approaches. Participants’ impressions were captured with questionnaires and interviews. Our results show a clear preference of the headphones over the smart glasses and signaling with intermittent audio while being in the dangerous area. However, we also found that participants’ acceptance of the approach was influenced by the additional perceived benefit the respective wearable would have in daily life. Using a wearable solely to be warned, although this would increase safety, was less acceptable. We discuss the implications of these findings for the design of cyclist warning systems.