Developing an efficient and sustainable precision irrigation strategy is crucial in contemporary agriculture. This study aimed to combine proximal and remote sensing techniques to show the benefits of using both monitoring methods, simultaneously assessing the water status and response of ‘Calatina’ olive under two distinct irrigation levels: full irrigation (FI), and drought stress (DS, -3 to -4 MPa). Stem water potential (Ψstem) and stomatal conductance (gs) were monitored weekly as reference indicators of plant water status. Crop water stress index (CWSI) and stomatal conductance index (Ig) were calculated through ground-based infrared thermography. Fruit gauges were used to monitor continuously fruit growth and data were converted in fruit daily weight fluctuations (ΔW) and relative growth rate (RGR). Normalized difference vegetation index (NDVI), normalized difference RedEdge index (NDRE), green normalized difference vegetation index (GNDVI), chlorophyll vegetation index (CVI), modified soil-adjusted vegetation index (MSAVI), water index (WI), normalized difference greenness index (NDGI) and green index (GI) were calculated from data collected by UAV-mounted multispectral camera. Data obtained from proximal sensing were correlated with both Ψstem and gs, while remote sensing data were correlated only with Ψstem. Regression analysis showed that both CWSI and Ig proved to be reliable indicators of Ψstem and gs. Of the two fruit growth parameters, ΔW exhibited a stronger relationship, primarily with Ψstem. Finally, NDVI, GNDVI, WI and NDRE emerged as the vegetation indices that correlated most strongly with Ψstem, achieving high R2 values. Combining proximal and remote sensing indices suggested two valid approaches: a more simplified one involving the use of CWSI and either NDVI or WI, and a more comprehensive one involving CWSI and ΔW as proximal indices, along with WI as a multispectral index. Further studies on combining proximal and remote sensing data will be necessary in order to find strategic combinations of sensors and establish intervention thresholds.