No matter what one thinks of the South, it is a place with a strong sense of place. And, this bond with a special locale is exemplified when artists unite and create images that promote a city as fascinating and distinct as Charleston. Both the native Charlestonian and the visiting artist, working roughly between the World Wars, played such a role. Embracing the historic ambience and desirable climate of South Carolina’s main seaport, the group helped to restore a thriving community and stimulate an active economy. As part of a larger cultural phenomenon—the Charleston Renaissance—the visual artists were joined with writers and musicians to reinvigorate the old American city with images that constructed a deep-rooted kind of southern charm. 1 Many of the works were designed for the tourist who was enchanted by the allure of the antebellum hub and its visual idiosyncrasies. Other works were part of an individual tour and expressed the creative inspiration gained from serendipitous travel. The main themes were depictions of renovated architecture, plantations, local inhabitants, and the nearby marshlands and rivers. Although unanimous in their attraction to the city, the artists were divided by their homeward origin. For the local artist, intimate with the city’s anguished past and present hopes, the art reflected a conservative taste, romantic aura, illustration, and picturesque charm. For the visiting artist, who, much like the average tourist, saw Charleston as an individual, fresh experience, the work revealed formal and iconographical experimentation with a drive toward personal expression and isolated mood. This chapter will discuss the effects of Charlestonian social values and influence with regards to the native versus visitor and the ultimate consequences that these distinctions had for the purpose and aesthetics of the visual product.