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Activity holidays in Greece

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.


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  
  • All accommodation
  • All continental breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking on Kythnos Island
Greece

Walking on Kythnos Island

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

JFMAMJJASOND

  • Holiday codeW06KY
  • Holiday typeSelf-guided walking
  • Duration6 nights, single centre
  • Activity level
  • Excellent for
  • From US$1249per person, tour only
  • NEW FOR 2023  
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Walking in the Outer Mani
Greece

Walking in the Outer Mani

Stay in traditional Greek accommodations as you explore the Peloponnese region, bursting with legend and plenty of varied walks.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07OM
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1399per person, tour only
  • NEW FOR 2023  
  • All accommodation
  • All breakfasts and 3 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Churches of the Peloponnese Walk
Greece

Churches of the Peloponnese Walk

Stay in the coastal village of Kardamili as you explore the unparalleled history and beauty of the Peloponnese.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07PE
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From Call usper person, tour only
  • NEW FOR 2023  
  • All accommodation
  • All breakfasts
  • Route notes provided
  • Flights from London (if booking incl. flights)
Walking on Kythnos Island - Premium
Greece

Walking on Kythnos Island - Premium

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

JFMAMJJASOND

  • Holiday codeW06KP
  • Holiday typeSelf-guided walking
  • Duration6 nights, single centre
  • Activity level
  • Excellent for
  • From US$1679per person, tour only
  • NEW FOR 2023  
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Walking the Pelion Peninsula
Greece

Walking the Pelion Peninsula

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

JFMAMJJASOND

  • Holiday codeW07GP
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1799per person, tour only

  • 6 Reviews
  • All accommodation
  • All breakfasts and 5 picnics
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Contrasts of Crete Walking
Greece

Contrasts of Crete Walking

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

JFMAMJJASOND

  • Holiday codeW07GI
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2049per person, tour only
  • All accommodation
  • All breakfasts
  • 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)
Mountains and Villages of Evia
Greece

Mountains and Villages of Evia

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

JFMAMJJASOND

  • Holiday codeW07EV
  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1849per person, tour only
  • All breakfasts, 4 picnic lunches, and 5 dinners
  • All accommodation
  • All transport and listed activities
  • Tour leader throughout
  • London flights (if booking incl. flights)
Walking on the Greek Islands
Greece

Walking on the Greek Islands

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

JFMAMJJASOND

  • Holiday codeW07GR
  • Holiday typeGuided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1899per person, tour only
  • All breakfasts
  • All accommodation (see below)
  • All transport and listed activities
  • Tour leader throughout
  • Flights from London (if booking incl. flights)
  • Arrival & departure transfers
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)