The Trigonio tower, constructed in the 15th century for fortification reasons, is part of the city walls of the old town of Thessaloniki. The tower is a cylindrical masonry building and has been considered as part of the cultural heritage of humanity by the UNESCO World Heritage Committee. Today it presents some major damage to its load bearing system, including intense cracking, moisture damage and disintegration of mortar, bricks and stones. An extensive research study for the evaluation of the tower’s bearing capacity, as well as for the suggestion of efficient strengthening interventions was held, in order to effectively prolong its expected lifetime. To this purpose, refined analytical models of 3D finite elements have been formed and used for the estimation of the elastic and inelastic tower’s response to gravity and seismic loads. Results’ evaluation of several static and dynamic analyses showed that the tower’s stability is not at risk under the action of gravity loads in general, but it’s bearing capacity under strong seismic excitations is questionable, thus becoming obvious the necessity of strengthening interventions. An invertible intervention of strengthening the tower with proper sets of external pre-stressed steel rings was also examined. Linear (elastic) analyses showed that they cannot sufficiently evaluate the effectiveness of this strengthening process. Inelastic analyses, using material laws of Drucker-Prager’s type, showed that the use of prestressed steel rings can significantly reduce the plastic strains’ appearance and therefore the cracking in the masonry walls of the monument.