In recent years, the urgent need to increase the safety standards of viaducts and bridges—under static and dynamic loading conditions—has required the development of advanced modeling approaches able to accurately predict the expected behavior of such infrastructures in a reliable manner. This paper presents a comparison between the adoption of a simplified modeling approach, widely used in the current practice, where the response of the structural system neglects the effects of the soil-structure interaction (SSI) phenomenon (considering the base of the structure fixed at the ground surface) and a rigorous modeling approach that considers the full 3D problem with all the components of the system (superstructure, foundation, and soil), through a finite element model. The pier of a real-world viaduct in central Italy was considered, with the aim of starting from a specific case study with foundation characteristics that are frequently found in viaducts in Italy, to obtain results that can be generalized to a wide range of similar types. Its behavior was evaluated both in the dynamic range of small oscillations and in the field of the seismic response to low and strong motion events. The results show that, in terms of seismic demand, the fixed-based model appears more conservative, but it significantly underestimates both elastic and residual displacements and rotations