A trip planning system may receive, from a user device, trip data identifying a starting point and a destination point for a trip and feature data identifying weights for trip features. The trip planning system may determine a geographical region of interest based on the starting point and the destination point. The trip planning system may receive viewpoint data identifying viewpoints located within the geographical region and may calculate, based on the feature data, viewpoint relevance scores for the viewpoints. The trip planning system may determine, based on the viewpoint data and the trip data, paths for the trip and driving times for the paths. The trip planning system may calculate an optimized path, from the paths, based on the viewpoint relevance scores and the driving times associated with the paths. The trip planning system may perform one or more actions based on the optimized path.