Precision Farming (PF) and Controlled Traffic Farming (CTF) are well known concepts within agriculture, but the adoption rate of these practices by farmers is still very low, because farmers lack the needed skills or fail to see the benefits of using these practices. If farmers want to reap the full benefits, operational planning must be carried out in advance for the entire crop cycle, before the crop season begins. However, operational planning across the entire crop cycle is a non-trivial task, since the efficiency of each operation is determined by a range of selected operational features (e.g., wayline direction, operational speed, vehicle capacity, wayline sequence, and turn type). To that end, we present, in this paper, an application that can support farmers with operational planning of field operations with CTF, by automating the process. It provides the farmer with an overview of all his field operations, and acts as a decision support tool during the operational planning process. The application allows farmers to store and manage field and equipment information, which is used as input, when setting up CTF and generating way lines and route plans for the individual fields. One of the key benefits of the application is the provided comparison feature, where farmers can compare alternative solutions, based on Key Performance Indicators (KPIs). Results from an example field, for operations with different machine setups, are presented to illustrate how KPIs and visualisations can support farmers during the decision process.