Today, many forms of art are influenced by the emergence of interactive technologies, including the mixing of physical media with digital technology for forming new hybrid works of art and the usage of mobile phones to create art projected on public spaces. Many artists and painters use digital technology to augment their work technically and creatively. In the same context many believe that the time of transition from traditional analogue art to post-modern digital art, that is, to an art grounded in codes rather than images has arrived (http://www.artnet.com/magazineus/features/kuspit/kuspit8-5-05.asp.). The research work described in this paper contributes towards supporting, through the use of Ambient Intelligence technologies, traditional painters' creativity, as well as methods and techniques of art masters. The paper presents the design and implementation of an intelligent environment and its software infrastructure, to form a digitally augmented Art Workshop. Its practical exploitation was conducted in an Ambient Intelligence (AmI) simulation space and four feasibility studies were conducted. In each of these studies an oil painting was created following an alternative, yet accredited by artists, approach.