Monitoring plant growth and development during cultivation to optimize resource use efficiency is crucial to achieve an increased sustainability of agriculture systems and ensure food security. In this study, we compared field monitoring approaches from the macro to micro scale with the aim of developing novel in vivo tools for field phenotyping and advancing the efficiency of drought stress detection at the field level. To this end, we tested different methodologies in the monitoring of tomato growth under different water regimes: (i) micro-scale (inserted in the plant stem) real-time monitoring with an organic electrochemical transistor (OECT)-based sensor, namely a bioristor, that enables continuous monitoring of the plant; (ii) medium-scale (<1 m from the canopy) monitoring through red–green–blue (RGB) low-cost imaging; (iii) macro-scale multispectral and thermal monitoring using an unmanned aerial vehicle (UAV). High correlations between aerial and proximal remote sensing were found with chlorophyll-related indices, although at specific time points (NDVI and NDRE with GGA and SPAD). The ion concentration and allocation monitored by the index R of the bioristor during the drought defense response were highly correlated with the water use indices (Crop Water Stress Index (CSWI), relative water content (RWC), vapor pressure deficit (VPD)). A high negative correlation was observed with the CWSI and, in turn, with the RWC. Although proximal remote sensing measurements correlated well with water stress indices, vegetation indices provide information about the crop’s status at a specific moment. Meanwhile, the bioristor continuously monitors the ion movements and the correlated water use during plant growth and development, making this tool a promising device for field monitoring.