Path planning in unstructured geographic areas usually cannot rely on an existing graph of potential route segments, but has to operate on polygonal spaces. Furthermore, it does depend on the underlying structure (e.g. terrain, weather, water conditions), which constrain the movement. When it comes to a reconstruction of historical ship voyages, exact trajectories or detailed navigation data are often lacking, and thus an accurate itinerary is difficult to reconstruct due to inaccurate or incomplete documentation. What is often given, however, are ship logs, which contain information about harbors, events on the route or general navigation information.</p> <p>The aim of this work is to determine potential navigation spaces that are based on the calculation of a geographical area that attempts to encompass all valid path options, based on given information and general assumptions also taking common navigational practices in historical seafaring into account. This knowledge is encoded in terms of different weighting schemes for a generalized shortest path approach. The idea uses the concept of <em>possibility spaces</em>, which was introduced in a previous publication (Fuest et al., 2025) and focused on the visualization of these uncertain spaces.