Maritime mobility has long been the predominant means of travel and transport. For millennia, ships have crossed the Mediterranean Sea for trade, migration, warfare, worship, pilgrimage, and cultural exchange. Yet this vast maritime landscape is also a place of loss. Thousands of ships have sunk in its waters and along its coasts, leaving a submerged archaeological record that remains only partially known due to logistical and economic challenges associated with extensive maritime excavations. Understanding where shipwrecking events were most likely to occur contributes to the scholarly study of ancient seafaring while also providing practical support for maritime archaeologists, developers, and cultural heritage managers in planning and optimising underwater archaeological surveys.This book explores the dynamics affecting seafaring practices in Classical times and the factors contributing to ship losses, asking where such losses were most likely to occur in antiquity. Focusing on Mediterranean territorial waters, it examines how environmental conditions, coastal geography, and human decision-making shape the risks of shipwrecking, particularly in coastal areas, where the safety of sailing near shore versus offshore remains controversial and widely debated. Grounded in archaeological and textual evidence, the study introduces a computational model designed to estimate the relative probability of shipwrecking across the Mediterranean. The analysis operates at two spatial scales. The first is a regional model focusing on navigation dynamics in the area between Cap Bon (present-day Tunisia) and Alexandria (present-day Egypt) during Roman times. This model is subsequently extended to all Mediterranean territorial waters in a simplified version, without chronological constraints. Particular attention is given to the role of risk perception and its possible divergence from actual nautical hazards—an aspect that has so far received limited attention but may have a significant impact on identifying areas with the lowest and highest probabilities of shipwrecking.