Artwork transportation processes are generally agreed-upon, and long running propositions between multiple partners that are specified over service level agreements, performance, and complex quality constraints to be maintained. The complexity of the constraints is defined by the sensitivity, value, and significance of artworks, where any recorded damage would probably leave undesired marks on the long-term, and diminish the lifetime of art pieces. Due to the uncontrollable, and unpredictable nature of the context during transportation, the specified constraints are often violated in real scenarios. In this paper, we introduce the PACT-ART architecture to integrate advanced computing techniques with transportation activities. This integration counts on external and Internet of Things (IoT) services to draw and understand the context of activities, thus it paves a way to predict a future state of the ongoing process and point out any possible violation in advance. Moreover, PACT-ART combines Complex Event Processing (CEP) techniques and makes this technology available even to non-experts in the domain. Finally, we showcase some initial experiments on real-life transportation scenarios that testify to the efficiency of our proposal.