Dynamic characterization is essential for understanding structural behavior and ensuring integrity. Structural Health Monitoring (SHM) using ambient vibration analysis offers a non-invasive, rapid, and effective approach for assessing historic structures. This study presents a case study on Venice’s historic masonry arch bridges, evaluating their structural conditions through synchronized Tromino sensors. These bridges are not only critical for pedestrian mobility but also represent valuable cultural heritage, making their preservation a priority. A network of Tromino sensors was strategically deployed on each bridge to capture ambient vibrations induced by wind, pedestrian traffic, and environmental factors. The recorded signals were processed using advanced spectral analysis and peak-picking techniques to extract key dynamic parameters, including natural frequencies, mode shapes, and damping ratios. These insights provide a deeper understanding of structural behavior, enabling the detection of potential damage and deterioration trends over time. Results confirm that ambient vibration monitoring is a reliable and effective technique for evaluating bridge conditions, offering early warnings of structural changes without invasive testing. The collected data also aids in the calibration of numerical models, improving predictive accuracy and facilitating Machine Learning applications for long-term structural health assessment. By applying this methodology to multiple case studies, this research highlights the potential of SHM in preserving cultural heritage. The proposed approach enhances structural evaluations, ensuring the longevity and safety of historic bridges while advancing modern engineering practices in infrastructure monitoring and conservation.