Cyclades walking & island hopping holiday, Greece

“Two weeks of guided walking around the Greek Cyclades islands, starting in Naxos and finishing in Santorini with lots of little ones in between. ”


Naxos | Mount Zas | Amorgos | Santorini | Iraklia | Koufonisi | Thirasia

Description of Cyclades walking & island hopping holiday, Greece

For an island hopping in the Cyclades Islands holiday, you can interchange your hiking shoes for water shoes as we discover the islands on land and on water. Starting in Naxos, the largest and most diverse Cyclades island, with high mountains including the famous Mount Zas, verdant valleys, traditional villages, ancient archaeology and long, sandy beaches to boot.

And with a two week itinerary on this Cyclades holiday, we have plenty of time to discover the big and small islands. Another biggie is Santorini, one of the most sought after island. It will take your breath away with its white Cycladic houses lining the cliff tops, in contrast with the dark, volcanic landscapes. Hiking here proffers amazing views either up to its great submerged caldera, or out to sea with spectacular sunsets never disappointing. It has ancient cities and villages for culture and stunning volcanic black and red beaches for nature.

This also leaves plenty of time for us to hop and hover over the Small Cyclades islands such as Amorgos, Iraklia or Thirasia. All very unspoilt, they are little bits of heaven and home to fine Greek hospitality and culture.

Our guided island hikes are graded as easy to moderate, walking mainly on paths of moderate gradient with ascents of up to 500m. We will walk up to 5-6 hours in the day including stops to rest and for lunch. And we always find you the finest places for lunch. These are the Greek Islands after all. However, if our guests would like a more flexible itinerary, with longer lunches and shorter walks, everything is possible. What isn’t possible is changing the weather. In August it is simply too hot to walk, and so we organise walking holidays in Greece all year round apart from the searing heights of summer.

Day-by-day itinerary

Day 1:Your island hopping in the Cyclades Islands holiday starts on Naxos where today you can settle in at our island guesthouse. With a briefing on our itinerary, history and culture of the islands, short walk around the historic old town followed by dinner at local taverna.
Day 2:Today our starting point for hiking is the idyllic island village of Apiranthos, with its Venetian tower, cobbled alleys and stone houses. From here, we hike to the summit of Fanari for a superb panoramic view of the Cyclades islands, trekking onwards through rugged, rocky terrain to the villages of Kaloxylos and Chalki. The former is filled with flower bedecked courtyards, and surrounded by an eclectic mix of both oak trees and olive groves. We finish our hike in Chalki at one of our favourite, locally owned organic restaurants.
Day 3:Today we’ll start our walk from the village of Filoti to take on the Cyclades Islands’ highest peak, Mount Zas (1,004m) named after the ancient Greek God Zeus who, it is said, spent his early life on Naxos. Certainly the summit views are verging on ethereal from the summit, with the Aegean glistening like heaven itself. Birdlife up at the top is impressive too, with great sights like the Griffon vulture soaring around the summit. And the end of day treat is the Zeus Cave, with superb stalagmite structures, followed by a well earned picnic and cool down at the island’s famous Argion water source.
Day 4:Yet another tranquil village, Koronos is our send off point today to discover more of Naxos’ remote, ancient mountain trails, where we can follow the scent of wild herbs such from lavender to thyme over hills and through valleys. When walking here in April and May we can also enjoy the explosion of wild flowers, with eighteen species of orchids alone on Naxos. This is also the time when the water starts to warm up, so you can enjoy a swim at the end of this trail at Lionas beach, followed by dinner at one of the island’s finest fish restaurants. .
Day 5:Today we head to a new island, Amorgos, which became world renowned after it featured in Luc Besson’s cinematic spectacular “Big Blue”. And Amorgos is spectacular. And surrounded by blue. All of which you can enjoy from our accommodation in the beautiful bay of Aegiali with sandy beaches, and pretty fishing port overlooked by four traditional villages poised up on the hills.
Day 6:Amorgos needs more than a day to enjoy, so today we start with exploring the narrow streets, ancient white stone houses, chapels and castle of the main village, the Chora. We’ll take the trail towards the famous monastery of Hozoviotissa, built into the cliff face and gleaming white in the sun. But every walk here has its shining stars, as we trek through the island’s core, passing medieval architecture, ancient villages, some now deserted, and unforgettable Aegean views. Finishing in the Bay of Aegiali, we dine at one of the oldest tavernas on the island.
Day 7:Another gift to walkers, Amorgos’ ancient circular path, adorned with wild flowers and herbs like a pretty natural necklace, takes us through the villages of Tholaria, Stroumbos and Langada. Dining at a local kafenio or café where the owners have a fine collection of local musical instruments, the violin and lauto. And with luck, we will get to hear them playing them too.
Day 8:Today we head to the third island of our holiday, this time one that is famous for its particularly crystal clear, turquoise waters - Koufonisi . So, as well as hiking around its coastal landscapes, our guests enjoy dipping in and out of its bays, literally.
Day 9:Today we travel to the most unspoilt island of the Small Cyclades; Iraklia, with a small population of 80 who welcome tourists with open arms as they arrive in the tiny fishing port of Ag. Georgios, with colourful fishing boats just adding to the delightful Aegean aesthetic. Our hike here is to the island’s highest peak, where you might spot the Griffon vulture as this is a favourite spot for breeding. And back at sea level, Maria’s Place is our favourite spot for eating, with plenty of Maria’s garden produce on the menu.
Day 10:Staying on Iraklia, we hike inland along ancient paths, passing the deserted village of Ag. Athanasios and then onto the spectacular Ag. Ioannis cave, the largest in the Cyclades Islands. We also hike to a secret beach only accessible by foot or boat to enjoy some beach bliss. And the evening brings another culinary highlight as we dine at the island’s best fish restaurant, where the catch of the day is caught by the owner.
Day 11:Today we head to the sumptuous island of Santorini, one of the Cyclades islands highlights for many. With plenty of time for walking left in the day, we start off in the picturesque port of Fira and follow a trail up to the rim of the island’s caldera to Oia, passing the picturesque villages of Firostefani and Imerovigli en route. This hike proffers a dramatic mix of cliffs, volcanoes and deep blue Aegean. With sunset at Oia, one of the best spots in the Cyclades to catch it, topped off with dinner at one of our favourite tavernas, with local wine and food at the heart of all their offerings.
Day 12:Our second day on Santorini, we hike a trail starting in the village of Emborio, up trough vineyard covered slopes to the Profítis Ilias summit (567m). With a perfectly placed monastery for a well earned snack and rest. From here we walk through elevated landscapes towards ancient Thera, one of Santorini’s greatest sites. And sights, with houses, a theatre, bath houses and roads dating back to the 9th century AD clinging to a 360m high ridge. We then descent to Perissa beach, with our usual end of day swim and supper.
Day 13:No Santorini holiday is complete without a visit to the volcano, and we take a boat there today followed by a short walk to the active crater. This is the newest volcanic island in the Eastern Mediterranean, and a fascinating place to visit. The volcanic activity has also created hot springs, of course, and there is nothing better after a couple of weeks of hiking to soak your body in sulphurous springs. We complete the day by taking another boat to the small island of Thirasia, another unspoilt gem, with a superb walk up 150 steps to the village of Manolas, with views back to the caldera and the nearby island of Thira.
Day 14:A final day to enjoy some of the best Greek island beaches, Thirasia’s being typically volcanic with black and red stones changing colours with each wave. Another option is to visit the ancient city of Akrotiri, buried by the eruption but now been excavated. And then onto to our farewell dinner in typical Cycladic culinary style. Plenty of local food and wine to toast your two week odyssey.

Hello. If you'd like to chat about this holiday or need help finding one we're very happy to help. Rosy & team.

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Check dates

2016: 5 Nov

Responsible tourism

Responsible tourism: Cyclades walking & island hopping holiday, Greece


We are dedicated to encouraging low-impact activity holidays, such as walking, and minimising our negative impact on the environment and people.

This walking trail holiday in the island of Naxos & the Small Cyclades in Greece, has an eco focus. We will inform our guests about the unique flora and endemic and common species they will encounter while walking or swimming around the island of Naxos, Amorgos, Iraklia, Donousa, Koufonisia. We give guidelines on where to look for them, how to approach them in order not to scare them and disrupt their life, how to observe their behaviours or even capture a unique picture showing to the rest of the world their magic. Guests leave aware of the environmental dangers faced and what they can do to minimise them.

We encourage our guests to behave in an environmentally responsible manner. We walk on designated paths and make sure no litter is left behind. We often arrange clean ups of paths and beaches during the week. We report on paths that are falling out of use and help to clear them.

We encourage our guests and the owners of the accommodations we use to be aware of the threats to the environment (i.e. water waste, plastic bags and bottles) and suggest ways in which they can minimise their negative footprint. We explain our guests the need for water conservation in the Greek islands and advise them on how to minimise their water waste. We encourage our guests to bring refillable water bottles and/or recycle them in designated areas. All our business waste is recycled. All communication is done electronically where possible, saving on paper.

We organise our walking holidays in Greece only for small groups of up to 8 people, outside the high season months of July-August. We thus try as much as we can to reduce negative impacts to the environment and its people and to benefit the local community.


We have the greatest respect for the local people and their customs and are anxious to share our knowledge of Cycladic island lifestyle with our guests. In order to limit the social impact of tourism all are guests are introduced to the local customs, religion, politics and history during our walks. We take our clients to local festivals, artists' workshops, and other locals celebrations trying to get them to experience the local way of life. We encourage our guests to mix and interact with the local people which are particularly friendly and hospitable.

Through our walking trail holidays in Greece we support small businesses by supporting locally owned shops, guesthouses, mini-markets, bakeries and taverns. As our holidays take place in spring, early summer and autumn, we bring customers and income to establishments which would otherwise only have visitors in high summer. Guests are advised to visit the local market and purchase locally-produced and home-made products such olive oil, wine, honey, capers and herbs, sun dried fruits and tomatoes, “louza” the local proscuito and other goods.

We buy food for our picnics from the local markets and prefer items locally grown according to the season, thus supporting the local agricultural community. Evening meals are taken in typical Greek restaurants serving local dishes.

Our guests stay at local, family owned guesthouses, staffed by locals with their food being sourced locally. These accommodations have been restored by local workers and retained their unique local character whilst providing all necessary comforts. The guesthouses recently installed solar panels which provide hot water for all rooms all year round.

Naxos & the Small Cyclades have a unique network of traditional walking paths and Annie and Andrea who will be your guides know them very well. They live and work in the area. They are passionate about promoting the Cyclades as a walking holiday destination, about the survival and conservation of the paths and local wildlife and sustainable tourism in general.

In general, with all walking holidays in Greece, we’re trying through our activities to encourage travellers to approach places they visits with greater understanding and respect.

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