Greece Adventure Holidays

Showing 10 out of 337 trips

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.

Greece

Cycling in the Peloponnese

£1239


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Greece

Cycling in Greece

£1829

 
 

VIEW TRIP

Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Greece

Walking on Kythnos Island

£739


5.0 (2 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

Greece

Cycling the Coast of Eastern Crete

£1119


4.0 (2 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
Navigation App

Greece : Peloponnese

Walking the Historical Paths of Outer Mani

£1189

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Greece : Peloponnese

Peloponnese Coast and Mountain Walking

£1209

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Greece

Walking on Kythnos Island - Premium

£1259


4.6 (7 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
Navigation App

Greece

Walking the Wonders of Crete

£1439

NEW FOR 2025

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Greece

Mountains & Villages of Evia

£1099


4.8 (4 reviews)

VIEW TRIP

Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

Printed route
directions

Greece

Walking on the Greek Islands

£1549

 
 

VIEW TRIP

Guided group walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

Tap here to filter results

Filter and sort

Holiday type
All

  • Self-guided walking
  • Self-guided cycling
  • Ski holidays
  • Canoeing
  • Multi activity
  • Pilgrimage
  • Private guided walking
  • Cultural tour
  • Guided group walking
  • Guided group cycling

Destination
Greece

  • Italy
  • Spain
  • France
  • Portugal
  • UK
  • Albania
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Costa Rica
  • Croatia
  • Cyprus
  • Czechia
  • Denmark
  • Egypt
  • Estonia
  • Finland
  • Germany
  • Gozo
  • Greece
  • Holland
  • Iceland
  • Ireland
  • Japan
  • Kenya
  • Malta
  • Montenegro
  • Morocco
  • Nepal
  • Norway
  • Peru
  • Romania
  • Slovenia
  • South Africa
  • Sri Lanka
  • Sweden
  • Switzerland
  • Thailand
  • USA
  • Vietnam

Departure month
All

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

Activty level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
All

  • Singles
  • Couples
  • Families
  • Food lovers
  • Wine lovers
  • Nature lovers
  • Bird watchers
  • Historic sites
  • Vegetarians
  • Swimming opportunities
  • Electric bikes
  • Tandem bikes
  • GPS navigation
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Unique accommodation
  • New holidays
  • Bestsellers

Sorted by


  • Price

  • Duration

  • Level

Update filters

 

Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.