This paper investigates how the overall pleasantness of the sound environment of an urban walking trip can be estimated through acoustical measurements along the path. For this purpose, two laboratory experiments were carried out, during which controlled and natural 3-min audio and audiovisual sequences were presented. Participants were asked to continuously assess the pleasantness of the sound environment along the sequence, and globally at its end. The results reveal that the global sound pleasantness is principally explained by the average of the instantaneous sound pleasantness values. Accounting for recency or trend effects improved the estimates of the global sound pleasantness over controlled sound sequences, but their contribution is not significant for the second group of stimuli, which are based on natural audio sequences and include visual information. In addition, models for global and continuous pleasantness, as a function of the instantaneous sound pressure level Leq,1s, are proposed. The instantaneous sound pleasantness is found to be mainly impacted by the average sound level over the past 6 s. A logarithmic fading mechanism, extracted from psychological literature, is also proposed for this modelling, and slightly improves the estimations. Finally, the globally perceived sound pleasantness can be accurately estimated from the sound pressure level of the sound sequences, explaining about 60% of the variance in the global sound pleasantness ratings.