The authors present the beginnings of a planning support system (PSS) for agri-environmental measures exemplified by a virtual implementation of Colorfields and blooming strips on model farms, based on real-world data. This paper starts with an introduction to the Colorfields, a concept for transdisciplinary and sustainable landscape design of set-aside land. Colorfields comprise of blooming strips of flowering annual or biennial plants, which are designed and drilled in pattern on fallow land creating Land Art. The temporary scenic arrangements of the Colorfields combine the advantages of ecological strips, e.g. providing habitats for insects (especially bees), improving soil fertility through the cultivation of intercrops, with improvements of the social recognition of farmers as producers of pleasant landscapes instead of monoculture fields. The prototype of the PSS uses two software tools of different scientific origin, the bio-economic modeling system MODAM and the landscape visualization system Lenné3D, which are linked based on geo-data. The resulting system helps to assess the economic effects and visualizes the effects of the specific landuse patterns under different scenarios. The economic assessment of blooming strips on arable land and of one Colorfield on fallow land shows that these measures prove to be profitable from an economic viewpoint assuming the current area payments for the obligatory European Union set-aside program. Furthermore, the visualizations enable the design to be tested virtually by exploring the resultant scenery. They provide artists, planners and stakeholders including farmers with a tool to virtually wander through landscape scenarios supporting a collaborative design and a shared vision for the community. The results of the two model farms and previous case studies for Colorfields demonstrate how current policy conditions could be used for the improvement of environmental and scenic qualities. Furthermore, the ability of the tools, MODAM and Lenné3D, suggests to support and promote these activities.