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Heavenly and Hellenic: walking on the Greek islands

Heavenly and Hellenic: walking on the Greek islands

It’s tricky to follow in the footsteps of Homer, Byron or Durrell when it comes to writing about the Greek Islands, as they’ve set the bar pretty high. You can, however, follow in their footsteps, as well as many others, along ancient footpaths scattered across an array of archipelagos. The word archipelago even comes from Ancient Greek, combining arkhi, meaning chief, and pelagos, meaning sea. In Ancient Greece, Arcipelago was actually the name for the Aegean Sea, where many of the islands lie, and the name was adapted with time to refer to a group of islands. In order to help you work out where to go walking on the Greek Islands, we have broken it down into archipelagos for you, then take you to the various Hellenic hiking heavens within. 

Cyclades Islands

This coastal cluster is a gift from the Greek gods and goddesses to all hikers. The Cyclades Islands archipelago is made up of 250 islands, islets and reefs, south-east of the mainland in the Aegean Sea. Its walking highlights include the highest Cycladic summit, Zas on Naxos (1,003m), the volcanic caldera on Santorini, or ancient paths across Paros and Syros. Bring binoculars and bathing suits, as coves and dolphins are omnipresent.

Hiking down to Aegiali Bay on the Cycladic island of Amorgos.


One of the smaller, lesser-known Cycladic islands, immerse yourself in Amorgos fully on a week of walking, covering the entire length of this narrow island. There is a healthy mix of ascents to remote monasteries and clifftop churches, as well as some deserted hilltop villages. There are also vibrant villages, such as Lagada, on the slopes of Krikellos, with its traditional whitewashed houses and labyrinthine streets, also home for our hikers for several nights. And, of course, there are beaches and bays with views of ‘the big blue’, which is also the name of an 1980s cult film shot here, directed by Luc Besson. 


This Cyclades island is the closest to Greece’s capital, just an hour by ferry from the small port town of Lavrio. It boasts an array of walking trails along ancient kalderimia to the likes of Otzia Bay, the ancient site of Karthaia and the elegant town of Ioulida. It’s so close that we combine your walking holiday with two days in Athens, exploring the city on a ‘hike and bite’ tour through not only some of the city’s ancient cultural highlights, but also its green and great gourmand spaces. Kea is the complete contrast of course, delightfully tourist-free, where you can explore the prettiest of pebbled beaches, unpretentious tavernas, salmon pink and white houses and a generous smattering of ancient towns such as the aforementioned Ioulida, Karthaia, Koressia, and Poiessa. 


Mythologically, Naxos nails it, as the island where Zeus grew up, and where he was given the gift of lightning by an eagle on Mount Zas, the highest peak in the Cyclades at 1,004m. Geographically it comes out top too, as it’s the largest of the Cyclades at 2,572 km2. Ancient to many but new to us, the island’s Naxos Strada trail, a blissful 52km coast-to-coast hiking trail over ten days, is one of our newest walking holidays on the Greek islands. As well as enjoying the contrasting landscapes of coast and mountainous hinterland, ancient sites and traditional villages, you trek to the summit of Zas (1,004m), with some fine views. Given that this island is said to have been blessed by Dionysus, the god of wine, also born here, and you’ll see many vineyards along the trail, you won’t be short of a local glass or two at the end of a day of glorious trekking. And, as mentioned above, you can also combine walks here with Santorini, on this tour

The Naxos Strada Trail on the island of the same name is Cycladic on steroids.


One of Greece’s most photographed islands, it is also one of the most populated by tourists, with cruise ships doing their fair share for overtourism. Walk away from the controversies and up to the colossal landscapes of its interior, such as Thira, the ancient capital of the island, following volcanic paths and vineyards through hidden villages. For Santorini at its most sublime, the 10km trail from the island’s capital Fira to Oia makes a fitting finale to our walking holiday there which is combined with the island of Naxos. Forget Insta, these views are forever-gram. And do try and travel outside July and August, when the temperatures are lower, and the crowds haven’t all landed yet.


Sifnos is another island idyll of blinding whitewashed houses and lanes, with blue doors and windows that contrast to perfection with the soothing shades of blue in every direction. Getting bored yet? Noone bores of Greek paradises like these, let’s face it. And you certainly won’t get tired of our carefully-crafted walking trails on Sifnos either. Based in the divinely beautiful Artemonas for the first four nights, walk through terraced hills, alongside mountain streams and to remote beaches, with the highest point, Profitis Ilias, 680m overlooking you along the way. Sacred sites are gorgeously Greek too, such as the Panagia Chrysopigi monasteries. The last two nights are in the coastal idyll of Kamares for some beach time. Or you can embark on one last trail, following an ancient donkey trail that connected Kamares with Apollonia, the island capital, taking in a 420m pass. (Don’t pass). 

Tinos and Andros

We’re pairing these two beauties together on this walking holiday, because they are just an hour apart, and yet offering a perfect meze of maritime trails. Andros is the starting point, just two hours from Rafina, a port town outside Athens, and is 40km from one end to the other. It has some exquisite elevations too, with its highest point on Mount Petalo at 997m. Our walks take you through the greener southern side of the island to the likes of Dipotama Gorge, along cypress-lined ancient trails and ubiquitous olive groves. You spend the second half of this week-long holiday on Tinos, which is larger at 197km². Here you have time in both the north and south of the island, giving you time to explore a fine range of its Hellenic hills, such as Exomvourgo (641m) as well as a maze of kalderimia, the traditional cobbled paths that feature on so many Greek islands. 

Another hike, another beautiful bay, on the island of Andros.

The Dodecanese and North Aegean Islands  

The Dodecanese archipelago is the southernmost group of Greek Islands, heading south-east towards Turkey. Their name translates as twelve islands, the dozen jewels including Patmos, Kos, Rhodes and Karpathos. Karpathos, is the second largest in the archipelago, the largest being Rhodes, where we don’t run walking holidays, but we do have a stunning cycling holiday. You can even combine this with our walking holiday on Karpathos. 


This is a very mountainous island and so, if you like your walking on Greek Islands to offer you a bit of a push, Karpathos kicks the proverbial. The highest peak is Kali Limni at 1,214m, which dominates the landscape on our Karpathos walking holiday. Spend a week exploring one of the most unspoilt of Greek islands, where villages are perched on craggy mountain sides or sprinkled along the coast. Follow ancient trails to the once Mycenaean city of Vroukounda, the traditional and folklore-filled village of Olympos or along the island’s mountainous spine with panoramic views across this Aegean arcadia. This island is also famous for its prolific mountain flowers, that peek through deep gorges and rocky coast, in places where botanists seek out endemic orchids. So if you come here in April, when the tour opens, it feels like the Greek gods have laid out a green carpet for you.  


Samos isn’t actually in the Dodecanese archipelago, but just north of it in the North Aegean. In its own little world, in fact, and quite out of this world too. Samos is also the birthplace of the ancient mathematician Pythagoras, but it has a very simple formula for making this one of the best places for walking on the Greek Islands. We have selected some spectacular walks on our Samos holiday, staying in three different places, north, west and south, so that you can trek to the finest of fishing villages, explore archaeological wonders such as Eupalinos Tunnel, dating back to 524BC, and end up at exquisite beaches such as Potami and Mikro Seitani. 

Karpathos is one of the most mountainous islands in the Dodecanese archipelago.

Ionian Islands

The Ionian Islands are west of the Greek mainland in the Ionian Sea, and they are home to some of the most famous of the Greek Islands, including Corfu and Kefalonia. Historically, they have been influenced by centuries of Venetian rather than Ottoman conquests, which has given them a slightly more European than eastern feel. 


A prime example of the archipelago’s Venetian past, Corfu’s fortified Old Centre, with three forts to protect its position and trading strength in the Ionian Sea, was constructed by Venetians and now protected by UNESCO. Its ancient heritage is scattered throughout this island however and, as one of the greenest of the archipelago, its natural heritage makes it a nirvana for hikers too. Which is why the famous British naturalist and writer, Gerald Durrell, lived here for many years. 

The Corfu Trail is one of the finest ways to explore the island, following a fairly strenuous 200km adventure into the heart of the archipelago’s second largest island. Walk it in segments or do the whole thing in two weeks, trekking up to the island’s highest point, Mount Pantokrator (905m), exploring the vast beaches and juniper dunes in the south, as well as the rugged gorges of the north. For a shorter walking holiday, follow in the footsteps of Gerald Durrell along the north-west coast and his home area at Kalami.

The Corfu Trail is one of the finest ways to explore the island, following a fairly strenuous 200km adventure.


Although Corfu may be more famous, Kefalonia is actually the largest Ionian Island, and more mountainous too. Mount Aenos is the tallest mountain at 1,628m, which is protected by a national park of the same name. At present, we don’t have walking holidays on Kefalonia, but we do take you cycling there, following trails along its limestone cliffs, cooling down at blissful beaches such as Myrtos or Antisamos and seeking out ancient sites and a vast array of remote villages. All in all, it feels like a gift from the gods. 


Kythira is the southernmost Ionian island, tucked off the Peloponnese Peninsula, just over an hour by ferry. It’s the meeting point of the Aegean, Ionian and Cretan Seas, so you are never short of views, with plenty of elevations to take them in. Hilly but not too mountainous, the highest point of the island is Mirmingaris (507m) but it is surrounded by hidden river valleys and waterfalls, a panoply of ancient sites and over thirty beaches. Our eight day walking holiday on Kythira is centre-based, staying inland in the village of Levadi, and car rental is included, so you can access the best trailheads at your own pace.

At the top of Mount Ainos, the tallest mountain on the Ionian island of Kephalonia.

Saronic Islands

The Saronic Islands are sailing central as their position in the Saronic Gulf, between the Attica Peninsula and the northeastern coasts of Peloponnese, is one of the closest aquatic havens for Athenian sailors. Made up of seven main islands, the Argo-Saronic archipelago, to give it its full name, also has superb hiking havens. We have walking holidays on three of them, which you could also combine with a walking holiday on the Peloponnese Peninsula. 


The largest of the Saronic Islands at 87km2, it was an important trade port in ancient times and consequently, the island still boasts an array of classical monuments, Byzantine churches, and elegant Neoclassical architecture. The most famous site is the temple of Aphaea, which is the grand finale of our four day walking holiday on the island. A short break, and a very chilled one, you are based in one hotel from which you have two terrific treks, including up to the island’s prettiest of peaks, Mount Ellanio (532m), with spectacular views across the Saronic Gulf. 

Hydra and Poros

We combine the two main islands in the Saronic archipelago into one walking holiday, as they are both strikingly different, while also simply striking. Poros is more forested, and Hydra more mountainous, the former famous for its aromatic pine groves that stretch down to its myriad bays. The second half of this walking holiday is on Hydra, a car-free island where the main port town is considered one of the most beautiful in Greece. It has preserved Neoclassical mansions, white-washed village houses and narrow cobbled lanes that climb steeply up from the horseshoe-shaped harbour. The beauty doesn’t stop there, however, as you will discover on coast to coast treks, with a water taxi to bring you back to base, or up to Mount Eros, the highest point on the island at 588m. 

It’s always important to stay Hydra-ted. As well as water, you’ll find vines at every turn on Hydra.


Last but definitely not least, we come to Crete. As this is the largest island in Greece, it sits proudly outside an archipelago all on its own, its White Mountains dominating the landscape from afar. Our self-guided walking holidays cover all compass points of this mountainous island. For example, you walk north to south through the White Mountains, Sfakia and Aradena Gorges on this epic Cretan adventure. And our East Crete walking holiday leads you through the Sitìa Geopark to some of Crete’s best beaches. These include Vai and Skinias, or a final walk in the Gorge of the Dead, bringing you out at the coastal village of Zakros. It’s so big, we needed a bigger blog, so you can read more about it here.