Lately, the music domain has been characterized by the appearance of innovative tools that are revolutionizing both the musicians’ way of playing and the musical instruments themselves. For instance, the Internet of Musical Things comprises smart musical instruments and devices that can communicate and control each other wirelessly, changing the musicians-instruments interaction completely. The present experiment analyzes the subjective experience , i.e., usability, user experience, and acceptance, of beginners and expert guitar players, considering three multi-effect pedalboards. These last comprised two prototypes, designed and developed for the study, that were characterized by a high level of personalization. Findings showed that more positive evaluations were assigned to the prototypes than to the traditional multi-effect pedalboard in terms of perceived ease of use, enjoyment, and intention of use. Furthermore, the study underlined the relevance of high customization in affecting the self -reported metrics. Indeed, in some circumstances, the most innovative prototype, i.e., completely wireless, received more favorable evaluations than both other musical devices.