The aim of this communication article is to present a successful irrigation advisory scheme on the island of Crete (Greece) provided by the Hellenic Agricultural Organization (ELGO DIMITRA), which is well adapted to the different needs of farmers and water management agencies. The motivation to create this advisory scheme stems from the need to save water resources while ensuring optimal production in a region like Crete where droughts seem to occur more and more frequently in recent years. This scheme/approach has three different levels of implementation (components) depending on the spatial level and end-users’ needs. The first level concerns the weekly irrigation bulletins in the main agricultural areas of the island with the aim of informing farmers and local water managers about crop irrigation needs. The second level concerns an innovative digital web-based platform for the precise determination of the irrigation needs of Crete’s crops at a parcel level as well as optimal adaptation strategies in the context of climate change. In this platform, important features such as real-time meteorological information, spatial data on the cultivation type of parcels, validated algorithms for calculating crop irrigation needs, an accurate soil texture map derived from satellite images, and appropriate agronomic practices to conserve water based on cultivation and the geomorphology of a farm are considered. The third level of the proposed management approach includes an open-source Internet of Things (IoT) intelligent irrigation system for optimal individual parcel irrigation scheduling. This IoT system includes soil moisture and atmospheric sensors installed on the field, as well as the corresponding laboratory soil hydraulic characterization service. This third-level advisory approach provides farmers with specialized information on the automated irrigation system and optimization of irrigation water use. All the above irrigation advisory approaches have been implemented and evaluated by end-users with a very high degree of satisfaction in terms of effectiveness and usability.