A range of remote sensing platforms provide high spatial and temporal resolution insights which are useful for monitoring vegetation growth. Very few studies have focused on fruit orchards, largely due to the inherent complexity of their structure. Fruit trees are mixed with inter-rows that can be grassed or non-grassed, and there are no standard protocols for ground measurements suitable for the range of crops. The assessment of biophysical variables (BVs) for fruit orchards from optical satellites remains a significant challenge. The objectives of this study are as follows: (1) to address the challenges of extracting and better interpreting biophysical variables from optical data by proposing new ground measurements protocols tailored to various orchards with differing inter-row management practices, (2) to quantify the impact of the inter-row at the Sentinel pixel scale, and (3) to evaluate the potential of Sentinel 2 data on BVs for orchard development monitoring and the detection of key phenological stages, such as the flowering and fruit set stages. Several orchards in two pedo-climatic zones in southeast France were monitored for three years: four apricot and nectarine orchards under different management systems and nine cherry orchards with differing tree densities and inter-row surfaces. We provide the first comparison of three established ground-based methods of assessing BVs in orchards: (1) hemispherical photographs, (2) a ceptometer, and (3) the Viticanopy smartphone app. The major phenological stages, from budburst to fruit growth, were also determined by in situ annotations on the same fields monitored using Viticanopy. In parallel, Sentinel 2 images from the two study sites were processed using a Biophysical Variable Neural Network (BVNET) model to extract the main BVs, including the leaf area index (LAI), fraction of absorbed photosynthetically active radiation (FAPAR), and fraction of green vegetation cover (FCOVER). The temporal dynamics of the normalised FAPAR were analysed, enabling the detection of the fruit set stage. A new aggregative model was applied to data from hemispherical photographs taken under trees and within inter-rows, enabling us to quantify the impact of the inter-row at the Sentinel 2 pixel scale. The resulting value compared to BVs computed from Sentinel 2 gave statistically significant correlations (0.57 for FCOVER and 0.45 for FAPAR, with respective RMSE values of 0.12 and 0.11). Viticanopy appears promising for assessing the PAI (plant area index) and FCOVER for orchards with grassed inter-rows, showing significant correlations with the Sentinel 2 LAI (R2 of 0.72, RMSE 0.41) and FCOVER (R2 0.66 and RMSE 0.08). Overall, our results suggest that Sentinel 2 imagery can support orchard monitoring via indicators of development and inter-row management, offering data that are useful to quantify production and enhance resource management.