UMapIT is an on-demand web mapping tool that is being developed in an attempt to provide Internet users with flexible means to personalize maps and interactively navigate within them. Based on a specific multiple representation database structure, it offers new functionalities to be applied at the occurrence level. These innovative functionalities come from the datacube paradigm. They include geometric drills which allow the user to navigate between the different LoDs (Level of Detail) associated to an object or to the different geometries of a same LoD that are aimed at different purposes. These functionalities also address the semantic and graphic aspects as well, offering further flexibility to the users interested in navigating among the different meanings associated to an object or change its visual variables (e.g. color, symbol) without affecting other occurrences of the same class. Furthermore, the underlying structure of UMapIT allows for the support of Â“GenZoomÂ” operations that adjust each objectÂ’s geometry individually according to the map scale, simulating on-the-fly cartographic generalization. The objective of this chapter is to illustrate the new capabilities offered by merging the datacube paradigm with an occurrence based approach for on demand web mapping. Emphasis is given to fundamental concepts and to their implementation into UMapIT. Such merging of GIS and datacube concepts, which emerged from the Business Intelligence (BI) field, has raised a lot of interest and research funding in Canada, reflecting the evolution going on in this country from spatial data management (using transactional systems) towards highly flexible spatial analytical systems (using geospatial intelligence technologies). This chapter also provides a solution the the desire of Canadian organisations to offer better map-on-demand web services.