The conservation of the Cultural Heritage (CH) requires, as preliminary but fundamental step, the collecting of different sources of information: from the historical evolution of construction and restoration works to the experimental data and monitoring systems. The handling of these information needs to an effective informative modelling, able to collect different type of data by using 3D parametric model. Historic Building Information Modelling (HBIM) can be considered a promising tool for the conservation of monuments which have to be protected along the centuries, due to its capability of archiving and handling the information about a building. This information model must be able to export the main structural information in the computational models with the aim to represent the connection between the real-world and the code output. The activities herein proposed, represent the research project CHARMING PISTOIA. Acronym of “Cultural HeritAge infoRmation ModellING for PISTOIA: from monitoring data to digital twin”; the goal of CHARMING PISTOIA is to deliver tools and methodologies to improve conservation of historical constructions by ensuring the optimal use of the resources required for the tasks of Control & Preservation. This is the scope of the project. It aims at establishing, through a three steps approach, a smart Digital Twin, i.e. a numerical model reproducing the structural behaviour of the physical system. Firstly, the design of the HBIM to collect the information on the structure and to export them in computational models. Secondly, the integration of a structural Health Monitoring (SHM) system to ensure the steady flow of structural information and its updating through Bayesian inference. Lastly, the definition of robust computational models for the Joint Vulnerability Assessment of the structure and the works of art inside. In this context, the Pieve of Sant’Andrea and its masterpiece, the Pulpit of Giovanni Pisano, represents an emblematic case study to meet the challenges of the research. In this paper the preliminary stages of the project are proposed through a detailed discussion of the expected results.