Multimodal traveling is expected to enhance mobility for users, reduce inequalities of car ownership, and reduce emissions. In the same context, ride-sharing aims to minimize negative impacts related to emissions, reduce travel costs and congestion, increase passenger vehicle occupancy, and increase public transit ridership when planned for first/last-mile trips. This study uses the empirical data gained from the pilot study in Athens, Greece, to outline a step-by-step planning guide for setting up a pilot study, and it concludes with challenges that emerged during and after its implementation. The demo aims to enhance the connection of low-density regions to public transport (PT) modes, specifically to the metro, through the provision of demand-responsive ride-sharing services. During the demo period, two different applications were utilized: the “Travel Companion” app and the “Driver Companion” app, which refer to passengers and drivers of the ride-sharing service, respectively. Demo participants were identified through a Stated Preference (SP) experiment. Challenges that were faced during the implementation show that although participants are willing to try new mobility solutions, the readiness and reliability of the new service are essential attributes in maintaining existing users and engaging new ones.