An itinerary proposal system includes: an accumulation unit that systematizes and accumulates itinerary samples, each of which includes a plurality of travel contents, on the basis of relevance of the travel contents; an extraction unit that searches for and extracts the itinerary sample that matches an inputted condition, from the systematized and accumulated itinerary samples; and a presentation unit that presents the extracted itinerary sample as a proposed itinerary. According to such an itinerary proposal system, it is possible to appropriately propose an itinerary that matches a traveler's condition.