Although the final definition of Archaeoastronomy is still under debate, what is clear is that this discipline offers a different approach to the knowledge of ancient cultures than traditional archaeology has done so far. Archaeoastronomy considers the sky as an inseparabe part of the environment and thus an element of the transformed landscape with highly symbolic content. In the case of the Roman culture, the great colonizing activity involved continuous spatial transformations and the skyscape should be considered as a piece of the created urbanized spaces. For this reason, a number of fieldwork campaigns were conducted in several Roman cities across different regions of the ancient Roman Empire in order to study the configuration of those landscapes and the possible integration of the sky during the buiding processes. At the present, our group has the largest sample of orientations of Roman settlements so far, and here it is shown the preliminary results of an statistical analysis which may offer new answers to the various still open questions in Roman urbanism, often faced from conservative views.