Historical cartography all over the world is a fundamental part of Cultural Heritage, and it needs to be preserved from damage of its analogical support due to ageing. Regeneration of ancient cartography in digital form is an interesting way not only to preserve historical cartographic documents as Cultural Heritage, but also to allow new chances of understanding and using the historical information they record. In such a way, modern digital techniques, in particular study of map deformations and map georeferencing, help in metric analysis of ancient cartography, and at last they appear to be useful for researchers to derive historical information for their studies, for example related to urban development or to geomorphological and environmental topics. The present research would give an example of the usefulness of the digital regeneration of ancient cartography, but also an example of possible difficulties in correctly interpreting information preserved in historical cartography, especially the pre-geodetic one. The study subject consists in three contemporaneous pre-geodetic maps (late 16th century) from the ancient Po river delta area (Italy), by means of which a geometrically correct representation of those parts of the landscape, not preserved today because of sea erosion, was tried. In fact, standard georeferencing methods, that use reference control points to compare historical cartography with the present one, in this specific case demonstrated to be not successful in describing the real location of disappeared landscape details with an adequate level of accuracy. For these reasons, in order to define which map among the others was the most faithful to the contemporaneous physical reality, a compound methodology, consisting of a three-step analytical process, is here applied to the three samples. Starting from measurement of sighting angles and distances applied to a number of landmarks, a splitting of the old maps in sub-areas, probably corresponding to the set of original surveyed zones, was performed. In the area of main concern, the use of absolute measurements was avoided in order to check the level of inner congruence of the representation. Finally, a new specific error index, that can also be applied to maps lacking an explicit graphical scale, is proposed to evaluate the map truthfulness degree. The proposed method can be applied to other similar examples from ancient cartography.