Ridesharing is part of the innovative shared transport regime which aims to maximize the utilization of mobility resources. Gaining knowledge of ridesharing’s impacts and how to assess them can significantly improve such services and thus contribute to their adoption among broader groups of travelers and to travel behavior change. This paper presents the framework deployed for assessing the impacts of a first-/last-mile ridesharing pilot in Athens, Greece, and capturing stakeholders’ (i.e., a researcher organization, a public authority and an infrastructure provider) point of view about planning objectives. Four impact areas are defined in total, and Key Performance Indicators (KPIs) are used. In parallel, in order to understand the stakeholder priorities when designing ridesharing services, the Analytical Hierarchical Process is implemented to estimate weights for each impact area. Increasing rail ridership is considered the top priority for all stakeholders during the planning phase for a first-/last-mile ridesharing service, which may have various implications for future initiatives. In total, 28 participants used the ridesharing service as drivers and passengers during the demonstration period. Results show that although a ridesharing service is expected to be an asset in daily transport for city travelers, the technological constraints currently burden its usage. However, as supported by demo results and travelers’ experience, there is great potential of ridesharing to contribute to a sustainable transport system and serve as a first- and last-mile solution to public transport.