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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.

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Cycling in the Peloponnese
Greece

Cycling in the Peloponnese

Explore the ancient history and archeaological sites of the Peloponnese on a 7 night self-guided cycling holiday. Starting near the mountains head towards the coast with the opportunity to visit Mycenae and Epidaurus. Cycling on quiet country roads through olive groves, traditional settlements and fishing villages.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07GP
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2299per person, tour only
  • NEW FOR 2023  

  • 4 Reviews
  • All accommodation
  • All continental breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Coast of Eastern Crete
Greece

Cycling the Coast of Eastern Crete

Cycle the tranquil coastline and historical sites of Eastern Crete. Stay in the bustling city of Heraklion before experiencing the beautiful villages of Agios Nikolaos, Ierapetra, and Rethimno.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07CT
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2099per person, tour only
  • NEW FOR 2023  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling in Greece
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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07GR
  • Holiday typeGuided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2379per 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)

    Cycling holidays in Greece

    Overall customer rating, based on 4 reviews