New media and devices are offering huge possibilities for the enhancement and the enrichment of heritage experiences, improving the users’ involvement. In particular, tourists equipped with their mobile devices are invading cultural attractions, sharing pictures and comments (together with hashtags and geo-localized positions) on social networks. These represent an unofficial source of data, which can be integrated with the official ones provided by GLAM (Galleries, Libraries, Archives, and Museums) and cultural heritage institutions, enriching them. At the same time, travel planners and mobile applications related to cultural heritage can play an interesting role in the development of smart cities, when they are integrated each other, engaging the user in touristic and entertainment activities, letting him/her be a source of cultural resources. This work focuses on equipping users (citizens and tourists) with a system providing support in computing personalized urban paths across cultural heritage places (monuments, palaces, museums, and other points of interest (POIs) related to cultural heritage in the urban environment) and in sharing multimedia resources about POIs, by exploiting gamification elements with the aim of engaging citizens and tourists. A mobile application prototype has been implemented, showing the feasibility of the proposed approach and exploiting crowdsourcing activities as a source of information for cultural places and works of art.