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In modern economies the possible application for autonomous mobile robots are manifold, ranging from warehouse logistics to domain specific applications like automated agriculture. A particularly interesting field in which to use autonomous robots is that of last mile delivery (LMD). Being the less efficient step in the entire delivery chain, LMD is looked at as a key factor for the success of any emerging or well established player in the e-commerce market. Using a fleet of sidewalks-navigating autonomous robots is often regarded to as a possible solution to the LMD problem. Given this context, this research aims at investigating the problems and possible solutions necessary to autonomously navigate an urban environment using sidewalks. A mobile robot called YAPE (Your Autonomous Pony Express) is used as a use case and a test platform for such techniques. The vehicle is a two wheeled, self-balancing one, and is equipped with a suite of sensors enabling autonomously driving a partially unknown environment. The control problems that are strictly related to such a configuration are investigated, with particular attention to the capability of the vehicle to overcome challenging terrains (pot-holes, steps, road irregularities). Localization, trajectory planning and tracking are also investigated, together with obstacle detection and avoidance techniques. Decisional logics to tackle problems that are peculiar of urban environments, like traversing crossings and navigating overcrowded sidewalks, are also developed.