Cultural heritage as a whole plays a significant role in the attractiveness of not only cities but also regions. On an international scale, it is used as a means to create an attractive image of places (branding) with the ultimate goal of revitalizing a place through an appropriate promotion of its image. The strategy of shaping the identity of a place emerges as a particularly critical issue in the present, taking into account mass migrations and supranationality. The contribution of monuments and archaeological sites to shaping the image of a place is taken for granted and becomes more important for areas that base their displaying on cultural heritage. However, the effects of such a policy cannot only be observed within a specific spatial context (city) but are able to extend to the regional level as well. The object of this paper is to map and justify the most significant archaeological sites and monuments of Larissa as a city and Thessaly as a region, in the framework of forming an attractive image of a potential tourist destination, depicting the efforts for their extroversion. In addition, the importance of space as an advantage in tourism planning is also highlighted.