Art and technology have always been very tightly intertwined, presenting strong influences on each other. On the other hand, technological evolution led to today’s digital media landscape, elaborating mediated communication tools, thus providing new creative means of expression (i.e., new-media art). Rich-media interaction can expedite the whole process into an augmented schooling experience though art cannot be easily enclosed in classical teaching procedures. The current work focuses on the deployment of a modern-art web-guide, aiming at enhancing traditional approaches with machine-assisted blended-learning. In this perspective, “machine” has a two-folded goal: to offer highly-interdisciplinary multimedia services for both in-class demonstration and self-training support, and to crowdsource users’ feedback, as to train artificial intelligence systems on painting movements semantics. The paper presents the implementation of the “Istoriart” website through the main phases of Analysis, Design, Development, and Evaluation, while also answering typical questions regarding its impact on the targeted audience. Hence, elaborating on this constructive case study, initial hypotheses on the multidisciplinary usefulness, and contribution of the new digital services are put into test and verified.