The paper addresses recent trends in the Motorways of the Sea (MoS) through an analysis of actions available to support and improve intermodal transport of people and goods among European and Mediterranean ports. It highlights public policy tools to back and finance MoS services in the European and Italian legal framework. It assesses how new technologies can be successfully deployed within the MoS related logistic chains, analyzing RFID, e-seals, port monitoring platforms, in the light of market needs for ITS. It discusses the design of port facilities in relation to MoS traffic. The paper deepens operational issues both on port side as well as on port inland relations, in economical and in technical terms. It deals with the Port of Livorno case, giving the chance to consider, in the real life of the leading Italian Ro-Ro port, the implementation of technological, operational and economic tools for MoS.