The research is aimed at using technological resources to form content and create a web resource, which is a digital guide. In determining the subject matter of the web resource, cultural objects that have different levels of preservation of the historical appearance of the area were considered. The selected areas are located within the borders of the city of Königsberg and have a density of pre-war buildings higher than the average density in Kaliningrad. To study the density, a GIS geographic information system was used, in which a layer was analysed in which polygon-houses with the first dates of mention or dates of construction were entered. The filtered layer was then matched with the repair and restoration data from the Capital Improvement Fund. In the final layer it was possible to determine the density of restored pre-war buildings in each district. Based on this analysis, routes between similar districts were selected. The quality of transport and pedestrian infrastructure and accessibility to architectural objects was studied separately when forming the concept of routes. The GeoDa programme searched for areas where the age of construction or first mention differed minimally. This parameter allows you to identify areas where buildings of the same or neighbouring eras are located. That is, in such areas the uniform historical style is minimally disturbed. Two districts were selected that fell within the city limits of Königsberger and fit the parameters outlined. The history of the creation of the districts, famous inhabitants, and main attractions were studied in detail. Based on this, two district itineraries were formed. On the web resource, the routes are presented as a guided tour of the district by its inhabitants.