A Visit to a Small Italian City is a quintessential example of Roger Brown making work for his own pleasure, as it encapsulates three of his great passions- travel, architecture, and medieval Italian painting. Brown was a lifelong and passionate traveler, his wanderlust taking him across the United States multiple times over throughout his life, and inspired a great deal of the content in his work. Brown also had a great love of architecture, related both to his travels and due to the fact that his partner George Veronda was a professional architect.

Perhaps most elusive, but also most visible throughout all his paintings, was Brown's love of medieval Italian painting. As a student of the Art Institute of Chicago, Brown obsessively studied the image-making strategies of pre-Renaissance painters, especially Giotto and Cimabue, and their isometric perspectives and archetypical figuration heavily influenced Brown's own signature style.

The circular, emanating clouds which fill the sky are slightly atypical for Brown but not entirely unseen in his career, employed most often to draw attention to a focal point, rather than unifying the overall picture plane. In this instance, the city becomes the clear subject of the piece, rather than an incidental feature of the landscape.