This paper explores solutions for characterising naturalness in relation to visual landscapes using Geographical Information System (GIS). It is argued that planners need to identify natural landscapes and monitor changes in their extent. Just like the indices that have been developed to describe the state of the economy, indices need to be developed that monitor the state of natural landscapes. The complications in characterising natural landscapes are outlined but it is argued that there is a need to develop definitions of natural landscapes that can be operationalised with a GIS. This will have the advantages of the efficiency of the technology and that the definition will be explicit and the implementation will be independent of the operator. Several GIS solutions are provided and these are an analysis of landcover, a density analysis of roads and utilities, and an analysis of property sizes. The analysis of property sizes is sensitive to many human modifications of the landscape because many developments begin with the subdivision of properties. However, it is argued in this paper that no one definition will suffice and that all three methods provide different, yet important, insights into natural landscape character. An aggregate classification of naturalness based on the majority value of the indices is demonstrated as well as a range of techniques for expressing the uncertainty of the aggregate classification.