Can a historical, analog site mapping tool be translated into a digital tool to change the way landscape is currently designed? This paper illustrates the path to the development of an on-site design tool and discusses its implications for landscape architecture. The presented field survey exemplarily illustrates an in situ design process from capturing georeferenced points, lines, and polygons in the field with a GNSS receiver and a tablet PC using the ESRI Collector app. By exchanging data with ArcGIS Online and translating the captured design parameters into three-dimensional outputs (in this case, trees) in ArcGIS Pro, visual feedback of the captured design points was generated while still in the field. The goal of this study is to strengthen the connection of landscape architectural design process to the site through the use of the in situ design tool. In the long term, the plan is to integrate the tool directly into CAD programs and to expand it to include applications in virtual and augmented reality.