Urban streets should be functional as both “path” and “place”, but “street as place” has been overlooked in urban design. The purpose of this thesis is to develop design guidelines for improving pedestrians’ experience on urban streets in Toronto. The study site is Gould Street in downtown Toronto. A preliminary study revealed thermal comfort, safety, social interaction and visual experience as key factors influencing pedestrians’ experience on urban streets. Design guidelines were formulated from literature review to address these key factors on Gould Street. These factors also form the framework for site inventories and analyses. The design concept, “Regenerating the river of life of the city”, is implemented by applying the guidelines to three design solutions. These alternatives were compared to identify their strengths and weaknesses related to the guidelines. Conclusions are drawn regarding the applicability of the guidelines, the limitations of the research and possibilities for future studies.