This article aims to assess the usability of selected map portals with a checklist. The methods employed allowed the author to conduct user experience tests from a longer temporal perspective against a retrospective analysis of the evolution of design techniques for presenting spatial data online. The author performed user experience tests on three versions of Tomice Municipality’s geoportal available on the Internet. The desktop and mobile laboratory tests were performed by fourteen experts following a test scenario. The study employs the exploratory approach, inspection method, and System Usability Scale (SUS). The author calculated the Geoportal Overall Quality (GOQ) index to better illustrate the relationships among the subjective perceptions of the usability quality of the three geoportals. The usability results were juxtaposed with performance measurements. Normalised and aggregated results of user experience demonstrated that the expert assessments of the usability of geoportals G1 and G3 on mobile devices were similar despite significant development differences. The overall results under the employed research design have confirmed that geoportal G2 offers the lowest usability in both mobile and desktop modes. The study has demonstrated that some websites can retain usability even considering the dynamic advances in hardware and software despite their design, which is perceived as outdated today. Users still expect well-performing and quick map applications, even if this means limited functionality and usability. Moreover, the results indirectly show that the past resolution of the ‘large raster problem’ led to the aggravation of the issue of ‘large scripts’.