Medieval Trails

Castles, beautiful princesses and pirates


On the northwest side of Kythnos island and perched at the summit of a steep rock, you will see the spectacular ruins of the beautiful Greek mediaeval castle of Kythnos, the "Kastro tis Orias". This pristine and completely unspoiled monument (no ticket kiosk, no tea shop, no information centre!) never fails to impress. It has a superb unhampered view of the Aegean, a diverse and attractive flora and fauna en route, and an unashamedly romantic history with the comings and goings of pirates, kings and queens!


Leaving the handsome northern port of Loutra, the unparallelled panorama of the eastern Cycladic islands is more than likely to take your breath away. As you continue hiking and ascend, you will relish the wild untamed scenery until you arrive at the mighty rock with its sheer cliffs, and the rugged Kastro clinging precariously to the top. Oria’s remains include the remnants of a settlement together with its enclosing walls. Of the one hundred churches that flourished in mediaeval times, only the church of Keraleousa and Agia Triada remain today. On the way back to Loutra, we go through entrancing and fertile farmlands that are a marked contrast to the starkness and grandeur of the Kastro.


  • 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


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


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


  • Standard: 45€ per person
  • Private: 55€ per person

Minimum participants: 3