Careful observation of the landscape can trigger multiple reflections and critical as- sessments. In fact, paraphrasing Le Corbusier, seeing is not a passive act, but already contains the kernel of a project. This profound, multisensorial relationship sparks a knowledge-gathering process leading not only to an appreciation of the uniqueness, identity and inimitable nature of the site, but also to comprehension of its cultural and historical importance and relative significance. Drawing can be used to analyse what has been built by the hand of man and what nature itself has created, record- ing how it has been affected by the passing of the years and natural and artificial events. All these drawings –some more technical, others more emotional- join forces to influence the conservation and enhancement of the landscape. Innovation –primar- ily guided by digital technologies- helps to convey environmental heritage as well as inspire choices regarding governance. These unique, multifaceted systems involving parks, urban centres, walkways, paths and rural landscapes could be managed as part of an Observatory on enhancement-oriented knowledge.