The Garisenda Tower, built in the XI century in Bologna (Italy) is a tilted Tower of 48 m high, with a square cross section, that represent the cultural symbol of the city. From the date of its construction, the tower was subjected to various accidents (such as fires, lightings and earthquakes) and interventions of consolidation. Nevertheless its structural configuration and the natural decay of the materials during the years, makes the tower inherently vulnerable to static and seismic actions, thus requiring a constant evolution of its structural health. The purpose of the study is to evaluate the current structural health of the Garisenda tower, through the development of a number of Finite Element models, in order to account for the influence of the geometrical configuration (actual inclination, cross section variability), peculiar construction techniques ("a sacco" masonry) and potential material degradation. To this aim, it has been of fundamental importance to integrate information related to both the actual geometrical configuration from data provided through static and dynamic monitoring and masonry texture, quality and material mechanical properties. In particular, to evaluate the effects caused by an eventual reduction in the material properties at the base, composed by selenitic stones, on the structural behavior, Three Dimensional Finite Element models with brick elements have been developed. The results of the FE analyses indicate that a material degradation at the base of the Tower could lead to local increase of stress levels close to material strength. Moreover, the analyses results also allow to better interpret some trends of behavior as resulted from the monitoring data.