This tour invites the visitor to the unknown heartland of Kythera and connects seven traditional settlements, two of which are listed due to their unspoiled architectural character. The siting and architecture of these settlements reveal the needs and the lifestyle of the residents in the past. Most of these villages were built to provide protection from the strong western winds as well as the frequent pirate raids which plagued the island during the Middle Ages. Starting from Palia Aroniadika, the old quarter of the village, the trail follows traditional handcrafted trails, navigating the hiker from one settlement to the other through rural landscapes sculpted by human presence: dry stone walling, threshing floors, pens and churches. These medieval settlements look like small forts, protected by perimetric buildings with reinforced walls and small windows. Inside the villages, the construction planning is ‘crammed’, as the building complexes are crowded together, and the public areas are confined to a few tiny plazas. The trail traverses the snake-shaped alleyways of the settlements, passing under kamares (archeways), next to sublime mansions, ruined “litrividia” (olive oil presses) and “kaminakia” (forges), which are all decorated with “poria” (type of travertine rock) and arched doors. In some abandoned houses, the stone ovens, the “lani” (winepresses), the stables, the inner courtyards as well as other parts of the house can be seen.