In this paper, we proposed personalized guided walking holidays in the city with wearable devices, which aim to provide a personalized service based on one's interest [Figure 1]. We firstly hypothesize that one's heart rate rises when he/she sees something he/she is curious about, and then test this using our developing prototype device. We conducted an experiment with four participants, in popular holiday walking areas such as Akihabara and Asakusa area in Tokyo. The data suggests that heart rate is significantly higher when participants see what they consider an interesting spot when compared with spots they are indifferent towards, implying that our concept is supported by quantitative physiological data responses. Perspectives of this research direction are discussed in terms of the relationship between city and human emotions.