The experiences gathered during the past 30 years support the operational use of irrigation scheduling based on frequent multi-spectral image data. Currently, the operational use of dense time series of multispectral imagery at high spatial resolution makes monitoring of crop biophysical parameters feasible, capturing crop water use across the growing season, with suitable temporal and spatial resolutions. These achievements, and the availability of accurate forecasting of meteorological data, allow for precise predictions of crop water requirements with unprecedented spatial resolution. This information is greatly appreciated by the end users, i.e., professional farmers or decision-makers, and can be provided in an easy-to-use manner and in near-real-time by using the improvements achieved in web-GIS methodologies (Geographic Information Systems based on web technologies). This paper reviews the most operational and explored methods based on optical remote sensing for the assessment of crop water requirements, identifying strengths and weaknesses and proposing alternatives to advance towards full operational application of this methodology. In addition, we provide a general overview of the tools, which facilitates co-creation and collaboration with stakeholders, paying special attention to these approaches based on web-GIS tools.