City monuments attract tourists, especially at places with efficient viewpoints. The conditions of visibility of eight historical monuments in the city of Bratislava were evaluated using GIS on a 3D landscape, employing the criteria of distance, impressiveness, size and the number of visible monuments. The visual quality of 15 selected viewpoints was verified by surveying more than 300 respondents about their views of the monuments from similar locations. These approaches allow us to assess the conformity of visual quality analysis conducted in objective and subjective ways. The most attractive viewpoints ranked by observers were remote from the historic town and provided views of several monuments, as well as a comprehensive panoramic view of the centre of Bratislava. The approaches to assessing visual quality analysis presented in this study represent a comprehensive way of defining and verifying which places are the best for effective sightseeing of a city’s monuments.