On a walking or cycling holiday in Greece with Headwater you will experience the more undiscovered corners that seem to sum up everything quintessentially Greek: remote monasteries and churches, ancient myths and legends, traditional mountain villages, remains of old buildings and hidden coves for swimming.
Our cycling holiday in Greece is based in the Peloponnese, a peninsula that will transport you right back in time to your schooldays when you learnt about the ancient Greek mythology. Whilst our walking holiday is based on the tranquil island of Evia, a place where the Greek people themselves holiday.
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
Embark on exceptional walks across the unexplored Cycladic Island of Kythnos. Filled with history and intrigue, this trip takes you to castles, churches, and caves. You’re spoilt for choice when it comes to stunning beaches, with plenty of spots to swim in the clear waters.
DEPARTURE MONTHS
Stay in traditional Greek accommodations as you explore the Peloponnese region, bursting with legend and plenty of varied walks.
DEPARTURE MONTHS
Stay in the coastal village of Kardamili as you explore the unparalleled history and beauty of the Peloponnese.
DEPARTURE MONTHS
Embark on exceptional walks across the unexplored Cycladic Island of Kythnos. Filled with history and intrigue, this trip takes you to castles, churches, and caves. You’re spoilt for choice when it comes to stunning beaches, with plenty of spots to swim in the clear waters.
DEPARTURE MONTHS
Walk on ancient cobbled trails to uncover the contrasts of the Pelion peninsula from the lush green mountainous interior to coastal trails on the Aegean Sea. Stay in traditional mountain villages and discover hidden coves, sandy beaches and picturesque fishing villages.
DEPARTURE MONTHS
This 7 night holiday in the south-west corner of Crete starts and ends in the historical city of Chania, takes in the Samaria gorge and the ruins of ancient Lissos and takes you on rocky coastal paths from one fishing village to the next.
DEPARTURE MONTHS
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
This trip offers the chance to experience Evia's magnificent mountain scenery. Routes have been chosen to showcase the best of the natural and historical sites on the island, including quaint traditional villages.
DEPARTURE MONTHS
Hopping from one wonderful island to the other, we enjoy a relaxed week of gentle walks through picturesque villages, lush valleys and sandy beaches.
DEPARTURE MONTHS
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
