Sustainable mobility is not merely a technological question. While automotive technology will be part of the solution, it will also be combined with a paradigm shift from car ownership to vehicle usage, which itself will be facilitated by the application of Information and Communication Technologies that make it possible for a user to have access to a mobility service from anywhere to anywhere at any time. Multiple Passenger Ridesharing and its variants appear to be one of the promising mobility concepts that are emerging. However, in implementing these systems while accounting specifically for time dependencies and time windows that reflect user needs, challenges are raised in terms of real-time fleet dispatching and dynamic route calculation. This paper analyzes and evaluates both aspects through microscopic simulation emulating real-time traffic information while also interacting with a Decision Support System. The paper presents and discusses the obtained results for a Barcelona’s Central Business District model. The obtained results prove the potential feasibility of the mobility concept.