Delivery systems are ubiquitous in today’s economy. However, those systems usually operate through purpose-built vehicles, which are inefficient, expensive, and highly harmful to the environment. We propose an optimal route crowd-shipping (OR-CS) system, a delivery service based on crowd transportation. The OR-CS system utilizes service points (SPs) and occasional couriers (OCs) to transfer deliveries. Senders drop packages at SPs, while receivers collect them from different SPs. The system is based on a new algorithm that assigns to each package an optimal route. The route is chosen individually for the package and is personally tailored according to the sender’s preferences and to the predefined routes of the OCs. To assess the real-life feasibility of the system, we developed a general simulator that emulates a city environment with authentic service points specifically selected based on desired attributes. The routes of OCs and the origins and destinations of packages were generated using a random process that differed between simulations. The results indicate that the system can be implemented and utilized. In addition, it yields positive results when the number of OCs surpasses a minimum threshold, which is feasible in most cities, given existing traffic loads. By adopting OR-CS, we can expect lowered delivery costs, reduced traffic congestion, and enhanced environmental sustainability.