This article investigates public spaces near urban rivers that contribute to the interaction between natural and urbanized areas and between people from different socio-economic backgrounds. The main goal of this study was to evaluate the environment of the largest urbanized areas of the Czech Republic, through which a large watercourse flows and creates a direct interaction with the city center. To evaluate the state of connectivity and comfort of urban rivers in the Czech Republic, a set of tools was applied to three cities: Prague, České Budějovice, and Hradec Králové. The methodology was created to correspond to the territory of Central Europe and was used for the specific assessment of rivers in four dimensions: (a) the spatial and visual accessibility, (b) the condition of the green corridor, (c) the condition of public space, and (d) the condition of the first built line. The dimensions are expressed using thirteen quantitative indicators of the environmental condition. The methodology uses the Urban River Sustainability Index (URSI), which was necessary to adjust the calculations of the indicators and resources for the Central European area. The best results were found in the central part of Prague and the worst in the peripheral part of Hradec Králové. The results call for the use of connectivity and comfort assessments of urban rivers for comparison, motivation, and future improvement in practice.