Feefo - Independent reviews
  Contact Us

Request a Brochure | Newsletter

Cycling holidays in Greece

An adventure like no other awaits with our cycling tours of Greece. A nation with a past based in myth and legend, cycling in Greece takes on a different form to many of our other tours, offering a glimpse of the glories of ancient Greek civilisation draped in a variety of breathtaking landscapes.

Our cycling trips across Greece take on handpicked routes chosen exclusively to display the magic of this historically rich and diverse land in all its glory. Read on to find out where exactly the magic of cycling in Greece lies.

Discover myth and mystery with our cycling tours of Greece

Our cycling holidays of Greece are based in the Peloponnese, a region home to much of the ancient country's myth and legend. Here, the goddess Hera is said to have bathed in the Canathus spring near what was once Epidaurus, now Epidavros. Nearby, Poseidon struck the ground with his trident and created a spring in Athens, while the attack against Troy was led from Mycenae in the Argolis region.

Everywhere you turn, Greece's glorious past makes itself known, offering fragments of temples by roadsides, upended capitals in sweet-smelling meadows and ancient stone bridges leading to hillside monasteries. And what better way to discover these remnants of a once great civilisation than on two wheels along winding and gliding trails.

Aside from being in the cradle of Greek civilisation, cycling in Greece also highlights the country's astoundingly beautiful countryside landscapes. Cycling holidays in Greece with Headwater will see you visit the main sights but will also reward you with stunning scenery that traverses thick pine forests, green vineyards, mountain streams and meadows bright with scarlet tulips and wild iris.

Along your stay you'll be treated to some of the region's most quaint and delightful stayover locations, with each of our packages available for upgrade, including the addition of extra nights and an electric bike. With Headwater cycling trips of Greece, it's up to you to set the pace of the adventure.

Book, travel and explore with absolute confidence on our cycling holidays of Greece

Your safety and comfort are always of paramount importance to us, however with COVID restrictions and regulations in a state of fluidity we have worked tirelessly to cover you against every eventuality in uncertain times.

If your trip need is cancelled at either end because of COVID, we guarantee a full refund via our comprehensive booking protection scheme. If you need to adjust your dates of travel, you can do so free of charge as close as 31 days to your initially proposed date of departure. We also offer our travel safety promise, which not only guarantees we will only provide travel to locations deemed safe, but also details our commitment to the highest standard of health and safety protocols within our cycling tours of Greece.

Our cycling holidays in Greece come naturally with safe social-distancing parameters, while the make up of our routes allows you to attack each day at a pace you feel comfortable. If you'd like to find out more, check out how we're making the experience of cycling in Greece safe and accessible amid COVID-19 regulations.

Read more▼

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
  • Activity level
  • Excellent for
  • From US$2749per 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)