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Cycling holidays in Greece

On a cycling holiday in Greece with Headwater you'll be based in the Peloponnese, the Greece of myth and legend: Hera bathed in the Carathus spring near Epidavros/Epidaurus; Poseidon hit the ground with his trident and created a spring in Athens; the attack against Troy was led from Mycenae. Everywhere its glorious past seems to overwhelm you: fragments of temples by roadsides, upended capitals in sweet-smelling meadows, ancient stone bridges leading to hillside monasteries.

Aside from being the cradle of Greek civilisation, the countryside here is astoundingly beautiful too. On a cycling holiday in Greece with Headwater you’ll visit the main sites, but also be rewarded with breathtaking scenery: thick pine forests, green vineyards, mountain streams and meadows bright with scarlet tulips and wild iris.

Cycling in Greece

Cycling in Greece

Our week of guided cycling is a journey through fascinating classical history and a superb variety of landscapes, from the azure blue of the sea to the green olive trees and vineyards of the heart of Greece.



  • Holiday typeGuided cycling
  • Duration7 nights, hotel-to-hotel
  • Excellent for
  • From £1479per person, tour only
  • Tour leader throughout 
  • All breakfasts 
  • Entrance fees to Acropolis and private guide
  • Support vehicle and driver
  • Local bike hire (e-bike can be requested, subject to availability, please inquire for prices)
  • Flights (if booking flight inclusive)