Hiking Medieval Trails at Kythnos island

A tour to the Medieval Kythnos with castles, beautiful princesses and pirates
View of the sunset from within the medieval castle of Kythnos
View of the sunset from within the medieval castle of Kythnos

Medieval Trails

Middle Ages had a profound impact on the island of Kythnos. Holidays in Kythnos island give you the opportunity to experience the dark ages of the island by hiking the Medieval Trails of Kythnos. Through this guided tour you will learn about glorious moments of the island and old stories which pass by word of mouth to the new generations.

One of the medieval landmarks of Kythnos is the Castle of Oria (or simply Kastro), located at the medieval capital, which lies on a steep cliff in the northwest of the island. An area with a tremendous view of the Aegean Sea, rich flora and fauna. This place is the center of a unique story which is lost in the depths of the ages with pirates, kings and beautiful princesses.

Taking selfies at the most stunning view of Cyclades


Our hiking experience begins above the settlement of Loutra in Kythnos island, giving a magnificent view of the eastern Cyclades. Then we continue uphill following a dirt road until we reach the junction that goes either north to the church of St. George or west to the Castle of Oria.

Further on our trail you may enjoy unique views of the western Aegean sea and the wild beauty of the landscape until you see the impressive steep cliffs where the Castle of Oria is built on. The Castle of Oria was the seat of the Italian feudal family of Gozzadini who dominated the island from 1337 to 1617 as the subordinates of the Venetian Duchy of Naxos. In 1292, Kythnos was plundered by the Catalans while throughout the Venetian and the Ottoman domination, it suffered greatly from pirate raids. Today, only the ruins of fortifying walls and medieval residences are preserved from the old Castle, while only the churches of Keralaousa and Agia Triada are preserved from its 100 churches.

After our guided tour and extensive storytelling at Castle of Oria, the hiking trail continues through the fruit crops of the locals and our experience ends at the port of Loutra.

The medieval trail offers a breathtaking view of the sunset in Kythnos


  • Starting time: 09:00am
  • Location: Upon request
  • Implementation period: All year round (upon request)
  • Trail distance: 12km
  • Route type: Circular
  • Activity duration with breaks: 4-5 hours
  • Difficulty: Moderate
  • Suitability: Suitable for all / relatively good fitness is required
Inside a medieval stone built arch


The altitude difference we cover is relatively smooth and only 4 km is uphill.

There is a minimum number of 4 participants required for the implementation of this outdoor activity. Experience Kythnos reserves the right to postpone or cancel the activity in case of non completion of the required number of participants. For individual bookings or for less than 4 participants please contact us to request a price.

Participants should have with them:

  • Bottle of water
  • Hat
  • Sun cream (during summer months)
  • Hiking shoes or trainers (open shoes, sandals or flip-flops are unsuitable)
  • Hiking backpack and poles (if available)
  • Swimwear and beach towels
Walking towards the medieval castle's gate


  • Guide
  • Tour planning - Sightseeing
  • Transfer from the exit point to entry point (if applicable)
  • Photographs from the tour
  • Liability insurance
  • All taxes


  • Standard: 50€ per person
  • Private: 60€ per person

Minimum participants: 3