Intending to safeguard architectural heritage, the assessment of the health of timber structures is crucial, though challenging, due to the organic nature of wood and to the uncertainties of its preservation state. To this end, useful support is provided by the ICOMOS guidelines, which provide conservation strategies based on thorough diagnosis and safety evaluations. In this context, the study summarized in this paper focuses on the medieval Tower of Montorio, which suffered considerable damage due to the strong earthquake that occurred in those area in September 2003. Its subsequent process of rehabilitation and restoration involved a widespread experimental campaign and the substitution of some timber beams. This circumstance has offered a rare opportunity to study these ancient elements in detail, although they are limited in number. Six beams made of oak and removed from an intermediate floor of the tower were evaluated through a comprehensive approach that included both non-destructive tests (NDT) and destructive tests (DT). Particularly, they were subjected to visual inspections, ultrasonic, sclerometric, and resistographic methods, and destructive four-point bending tests. Overall, the study presented here provides a useful qualitative comparison between them. Results highlighted that relying only on NDT might lead to an overestimation of mechanical properties and that combining NDT with DT is crucial for a more accurate assessment. Therefore, the need to deepen the research on correlations between NDT and DT to obtain reliable values of mechanical properties while respecting the conservation aim was confirmed.