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.


Why choose Headwater?


Cycling in the Peloponnese
Greece

Cycling in the Peloponnese

Embark on an exhilarating cycling tour through the heart of Greece's Peloponnese region. Pedal diverse terrains - mountains, coast, ancient cities, and charming seaside towns. Explore historical treasures such as Mycenae and Epidaurus, pausing for authentic Greek delights.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07GP
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2750per person, tour only

  • 5 Reviews
  • 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

Experience 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$1640per person, tour only

  • 2 Reviews
  • 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

Step into the enchanting realm of Greece's Peloponnese on a walking holiday, tailored for enthusiasts of authenticity, nature, food, and history. Follow ancient 'Kalderimi' mule paths, tracing Byzantine chapels and scenic gorges. Dive into history and nature, from coastal trails to the renowned Dirou Pirgos caves.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07OM
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1700per person, tour only

  • 1 Reviews
  • 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

Uncover the Peloponnese's Charm! Walk through Kardamili and the secrets of Outer Mani, discovering 30 ancient Byzantine churches. Stroll along the foothills of the stunning Taygetos Mountains and explore the coastline. It's a perfect mix of mountain and coast, where you can enjoy local food and embrace Greece's heritage.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07PE
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1820per person, tour only
  • All accommodation
  • All breakfasts
  • Route notes provided
  • Flights from London (if booking incl. flights)
Walking the Pelion Peninsula
Greece

Walking the Pelion Peninsula

Walk along ancient, cobbled trails to explore the Pelion Peninsula's contrasts, from lush green mountainous interiors to coastal paths bordering the Aegean Sea. Experience the essence of traditional mountain villages and uncover hidden coves, sandy beaches, and charming fishing villages.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07GP
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1925per 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

Discover the enchantment of Crete on our walking tour, tailored for nature lovers and food enthusiasts. Wander ancient shepherd trails, delve into vibrant gorges, and explore hidden coastal gems in the tranquil southwest corner. Indulge in Cretan delights, encounter wildlife, and unwind in charming seaside hotels.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07GI
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2300per person, tour only

  • 2 Reviews
  • 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

Embark on a scenic cycling tour through Eastern Crete, exploring picturesque villages and golden beaches. Indulge in local delights, all while pedalling along the stunning coastline. Stay in charming family-run accommodations and witness the island’s rich biodiversity. A perfect blend of nature, culture, and gastronomy.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07CT
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2390per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)