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

CA$2555


4.8 (11 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Greece

Cycling in Greece

CA$3480

 
 

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Guided group cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Greece

Walking on Kythnos Island

CA$1605


5.0 (2 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
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Greece

Cycling the Coast of Eastern Crete

CA$2330


4.0 (2 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 3
Stretching

Headwater
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Greece : Peloponnese

Walking the Historical Paths of Outer Mani

CA$2460

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Greece : Peloponnese

Peloponnese Coast and Mountain Walking

CA$2500

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
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Greece

Walking on Kythnos Island - Premium

CA$2595


4.6 (7 reviews)

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Self-guided walking

6 nights,
twin centre

Level: 2+
Moderate plus

Headwater
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Greece

Walking the Wonders of Crete

CA$2935

NEW FOR 2025

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Self-guided walking

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
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Greece

Mountains & Villages of Evia

CA$2090


4.8 (4 reviews)

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Guided group walking

7 nights,
single centre

Level: 2+
Moderate plus

Printed route
directions

Greece

Walking on the Greek Islands

CA$2945

 
 

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Guided group walking

7 nights,
hotel-to-hotel

Level: 1
Leisurely

Printed route
directions

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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.