Water losses from water distribution means have a high environmental impact in terms of natural resource depletion (water, energy, ecosystems). This work aims to develop an optical airborne surveillance service for the detection of water leaks (WADI—Water-tightness Airborne Detection Implementation) to provide water utilities with adequate and timely information on leaks in water transportation mains outside urban areas. Firstly, a series of measurement campaigns were performed with two hyperspectral cameras and a thermal infrared camera in order to select the most appropriate wavelengths and combinations thereof for best revealing high moisture areas, which are taken as a proxy for water leakage. The Temperature-Vegetation-Index method (T-VI, also known as Triangle/Trapezoid method) was found to provide the highest contrast-to-noise ratio. This preliminary work helped select the most appropriate onboard instrumentation for two types of aerial platforms, manned (MAV) and unmanned (UAV). Afterwards, a series of measurement campaigns were performed from 2017 to 2019 in an operational environment over two water distribution networks in France and Portugal. Artificial leaks were introduced and both remote sensing platforms successfully detected them when excluding the unfavorable situations of a recent rain event or high vegetation presence. With the most recent equipment configuration, known and unknown real leaks in the overflown part of a water transportation network in Portugal have been detected. A significant number of false alarms were also observed which were due either to natural water flows (groundwater exfiltration, irrigation runoff and ponds) or to vegetation-cover variability nearby water-distribution nodes. Close interaction with the water utilities, and ancillary information like topographic factors (e.g., slope orientation), are expected to reduce the false alarm rates and improve WADI’s methodology performance.