Historical city centres face two major challenges in the 21st century: heritage conservation and energy retrofitting. Wall insulation in traditional buildings is at the crossroads of these two issues. When studying the retrofit of the walls, other factors also need to be considered, such as the durability of the walls, the life cycle of the materials used for insulation, the indoor and outdoor comfort in summer. The aim is to propose a method for taking all these objectives into account when choosing the insulation technique for historical walls. To do this, the TEB (Town Energy Balance) urban climate model is used, because it considers the urban microclimate, the energy behaviour of buildings and moisture transfer through walls. A VTT model is integrated into TEB, to include the risk of mold growth. The medieval city centre of Cahors (France) was used as a case study. The retrofit of two types of wall was assessed: “massive” brick walls, and “light” walls with a timber-framed structure, filled with bricks. Six renovation scenarios were studied, including four insulation materials and both internal and external insulation positions. The results obtained underline the need to study the retrofit of the two types of building separately, because the recommendations made for insulation vary depending on the type of wall studied.