Sea level rise and high tide events are threatening many coastal cities, which require adequate and sustainable protection measures. The historic city centre of Venice (Italy) is often flooded during very high tide events, especially the area of St. Mark's island, which is at the lowest elevation among all the islands forming the city. In order to design cost effective protection interventions to safeguard the historical heritage, a deep understanding of flooding mechanisms and the relationship between groundwater pressure and tidal oscillations are necessary. Geotechnical survey and analyses play an important role in this process. This paper presents the results of a recent monitoring campaign carried out in St. Mark's island. A simplified one-dimensional analytical model has been derived for saturated conditions to understand the key parameters that govern tidal induced pressure oscillations in soil (material properties, geometrical features and wave properties). Additional features, such as partially saturated soil conditions and twodimensional effects, have been investigated numerically. Results show that significant pressure oscillations occur in the subsoil, which should not be neglected for the stability of horizontal architectural structures, such as the historical mosaics and paving. However, seepage flow rate is small, thus its impact on the drainage system is limited in terms of water discharge.