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.
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. Each night, relax in meticulously selected hotels, merging luxury with Peloponnesian tranquillity.
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
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. Experience the magic of ancient civilisations, inviting curiosity and sparking your adventurous spirit.
DEPARTURE MONTHS
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
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 adventure, where you can enjoy local food and embrace Greece's heritage.
DEPARTURE MONTHS
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
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. Every step reveals the diverse beauty of Pelion, making each moment a unique discovery.
DEPARTURE MONTHS
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. Start in Chania, amid the White Mountains' beauty. Indulge in Cretan delights, encounter wildlife, and unwind in charming seaside hotels. Embrace the serenity, savour exquisite food, and immerse yourself in a walking adventure where every step tells a tale.
DEPARTURE MONTHS
Embark on a scenic cycling tour through Eastern Crete, exploring picturesque villages and golden beaches. Indulge in local delights, from signature cheeses to Raki, 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 makes this cycling holiday unforgettable.
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
