Martial incidents during wars (World War I and II), but also shipping fatalities through centuries along the densely populated commercial routes of the Mediterranean Sea have resulted in significant submerged remnants, falling into the Underwater Cultural Heritage (UCH) corps. A large part of this heritage is located in the neighborhood of insular territories. Preservation and sustainable exploitation of this UCH in the Mediterranean presents an important opportunity for both keeping alive the European identity for future generations, and tracking alternative, heritage-led future development trails for remote peripheral and lagging-behind island communities. The paper explores the context of UCH in the Mediterranean and elaborates on the value attached to Information and Communication Technologies (ICT) for reaping this opportunity by means of surveying, geolocating, preserving, sustainably exploiting and marketing this heritage. Based on this exploration, but also on the authors’ experience from a specific (U)CH-related cultural planning endeavor, conducted in Leros Island Greece, ICT and non-ICT related barriers for planning heritage-led future trails of insular regions are delineated.