The application of retrofit actions to existing building stocks can improve the energy performance of the residential sector. In this context, particular attention should be given to historical buildings, which represent a large part of the Italian building stock. To improve the energy performance of them, adequate retrofit actions must be applied. Many studies and regulations have focused on identifying the best refurbishment measures. However, the selection of these measures is difficult due to restrictive regulations, which are dictated by the Ministry of Cultural Heritage and Activities, high retrofit costs, and variable climate zones. Thus, energy renovations in Italian buildings are not simple, and it is very difficult to find generic solutions that can be applied to buildings across the entire territory. In this paper, the authors investigated the most common retrofit solutions used in Italy, focusing in particular on the energy performance of historical building envelopes. First, energy performance analyses were conducted for two typical base cases in four different Italian cities using TRNSYS software, and some common retrofit measures were analysed. In some cases, the results showed Primary Energy saving of 44.6% (sample A) and 56.7% (sample B). Furthermore, these were used to identify different energy and economic impacts associated with the same refurbishment measures in different climatic contexts, highlighting the non-existence of a generic solution suitable for all regions or countries.