The upcoming Fluorescence Explorer (FLEX) mission will provide sun-induced fluorescence (SIF) products at unprecedented spatial resolution. Thus, accurate calibration and validation (cal/val) of these products are key to guarantee robust SIF estimates for the assessment and quantification of photosynthetic processes. In this study, we address one specific component of the uncertainty budget related to SIF retrieval: the spatial representativeness of in situ SIF observations compared to medium-resolution SIF products (e.g., 300 m pixel size). Here, we propose an approach to evaluate an optimal sampling strategy to characterise the spatial representativeness of in situ SIF observations based on high-spatial-resolution SIF data. This approach was applied for demonstration purposes to two agricultural areas that have been extensively characterized with a HyPlant airborne imaging spectrometer in recent years. First, we determined the spatial representativeness of an increasing number of sampling points with respect to a reference area (either monocultural crop fields or hypothetical FLEX pixels characterised by different land cover types). Then, we compared different sampling approaches to determine which strategy provided the most representative reference data for a given area. Results show that between 3 and 13.5 sampling points are needed to characterise the average SIF value of both monocultural fields and hypothetical FLEX pixels of the agricultural areas considered in this study. The number of sampling points tends to increase with the standard deviation of SIF of the reference area, as well as with the number of land cover classes in a FLEX pixel, even if the increase is not always statistically significant. This study contributes to guiding cal/val activities for the upcoming FLEX mission, providing useful insights for the selection of the validation site network and particularly for the definition of the best sampling scheme for each site.