The Coastal Transport Information System (Co.Tr.I.S) is a multifunction information system that is developed for the effective design of coastal transportation lines. The system incorporates several subsystems which include the models, tools, and techniques that support the design of improved coastal networks. Co.Tr.I.S main aim is to support any decision making process of the involved players (Ministry, Maritime companies, Local Authorities, Travel Agencies, Passengers, etc) regarding the improvement & the optimal use of a coastal transport network. Co.Tr.I.S data retrieval, analysis, visualization, network design & decision support can accelerate the very slow (currently annual in Aegean) rate of coastal transport network update/upgrade procedures, and, create smarter network implementations that may adapt online on the various demand or requirement changes or updates. Connections, transportation, mobility, as well as port automation are some of the key factors for the “smartification” of entire islands especially in an archipelago like the Aegean Sea. In this work, we present the network design optimization functionality of Co.Tr.I.S, the various optimization stages, the Genetic Algorithm (GA) implementations and its potential to propose a better network design based on each user preferences. A sample case study is given to show its smartness & adaptability to each user needs and, finally, a discussion follows on how it could be complemented by emerging smart technologies for smarter islands.