Back in the old times, before the use of cars, the trails would link different destinations. The shorter and the easier a trail was, it was considered as a good trail. Nowadays, trails are mainly used from hikers. A trail now is considered as good, depending on its richness in cultural monuments and natural sites. Like Ulysses trip, the Odyssey, trails today are a trip in time. In the past and in the future. The richer a trail is, the richer the experiences the hiker will gain when arriving at the end. In October 2015 we visited Ithaca, the mythical island of Ulysses. Our aim was to investigate the possibility of creating a hiking trails network on the island. We were very impressed by the access to the numerous historical sites, the internationally famous mythology that is linked to many places encountered while walking, we greatly appreciated the antithesis of landscapes and colors as well as from the friendliness of people. The trails we hiked form an extensive network that, if well organised, could work as an attraction for a great amount of hikers worldwide.