Walking holidays in the Cyclades
trails of light between white villages and turquoise sea

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Giovanna Crippa

Product Manager Europe

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David Praire

CEO

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Kristiina Gaillard

Greece & Mediterranean specialist

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The finest Cyclades islands on foot

Each island has its character, its paths, its flavours. Here are those our walking holidays invite you to discover, step by step.

Sifnos

The gastronomic capital of the Cyclades, Sifnos is also a walker's paradise. Its paved kalderimia link some thirty villages punctuated by more than a hundred chapels and pottery workshops. You walk in the morning between hilltop monasteries, lunch on revithada slow-baked overnight in a wood-fired oven, and spend the afternoon with your feet in the water of a turquoise cove.

Serifos

More secretive, less frequented, Serifos offers that rare feeling of having an island to yourself. Its Chora, considered one of the most beautiful villages in the archipelago, overlooks terraces of olive trees cascading towards the blue Aegean. The paths cross former mines and trace wild coves where silence is broken only by the song of cicadas.

Naxos

The largest of the Cyclades is also the most generous. Mount Zas (1,004 m), the highest point of the archipelago, looks down over fertile valleys planted with citrus and olive trees. Mountain villages (Halki, Filoti, Apiranthos) preserve an atmosphere of deep Greece, between Venetian towers, flower-filled lanes and terroir cheeses.

Amorgos

Wild and unspoilt, Amorgos is the island of The Big Blue. The monastery of Panagia Hozoviotissa, clinging to a vertiginous cliff, is one of the most striking monuments in Greece. The walking paths cross arid, grandiose landscapes, punctuated by isolated chapels and turquoise coves.

Santorini

Beyond the sunsets, Santorini lends itself beautifully to walking. The ridge trail between Fira and Oia runs along the volcanic caldera with a breathtaking panorama. The Assyrtiko vineyards, trained in low baskets on volcanic soil, and the archaeological site of Akrotiri complete a singular picture.

Milos

Its wind-sculpted white cliffs at Sarakiniko, its sea caves at Kleftiko and its colourful fishing villages (the syrmata) make Milos an island apart. Coastal paths offer a complete change of scenery, between near-lunar rock formations and coves of crystalline water.

Guided or self-guided: two ways to walk the Cyclades

Guided journeys

An English-speaking guide who knows each island inside out, a small group of epicurean travellers, tavernas that only locals frequent: our guided trips turn walking into an art of living. Transfers, charming addresses and ferry crossings are orchestrated so you have nothing to do but savour the path.

Self-guided holidays

A detailed road book, boutique hotels booked at every stage, your luggage waiting on arrival: freedom without the unexpected. You shape your days as you wish, walk at your own pace, linger in a village that appeals. And our team is reachable at any time.

When to walk in the Cyclades

Spring (April to June) is the ideal season: hillsides blaze with wildflowers, the light is soft, temperatures perfect for walking. The islands live at their natural rhythm, far from the summer influx, and the first swims in an already-tepid sea punctuate walking days.

Autumn offers an incomparable light, lower, more golden. The sea, warmed by summer, invites post-walk dips. Tavernas serve fresh figs, capers of the season, grapes just harvested. October in the Cyclades is the best-kept secret of travellers who love to take their time.

What sets Kelifos apart

Since 1983, we have been designing walking holidays in Greece with the attention to detail that changes everything. Charming addresses chosen one by one, luggage transferred from stage to stage, English-speaking local assistance, guaranteed departures so you travel with peace of mind. Our advisors, with deep knowledge of the archipelago, help you choose the itinerary, the islands and the season that suit you best.

Frequently asked questions about walking in the Cyclades

Which Cyclades island should I choose for walking?

It all depends on the atmosphere that draws you. For fertile valleys and mountain villages, we love Naxos and its Mount Zas; for wild landscapes and clifftop chapels, Amorgos has no rival; food lovers savour Sifnos and its paved paths, while confidential Serifos and Milos with its lunar coves reward those looking for quiet. Our advisers will gladly steer you towards the island, or the combination of islands, that suits you.

Should I choose a guided or a self-guided holiday?

Both formulas offer the same comfort — it is the tempo that differs. On a guided trip, an English-speaking leader opens up the lanes, the bread ovens and the tavernas that only regulars frequent, within a small group of epicureans. Self-guided, you move at your own will with detailed route notes and the track for each stage, without having to prepare a single map yourself; the local Anavasi maps remain a lovely complement for dreaming up the itinerary. In both cases your luggage travels from hotel to hotel and our team stays reachable.

Can you link several islands together on foot?

Yes, and that is the whole charm of the Cyclades: you pass from one island to the next by ferry, bags dropped off, savouring the crossing as a stage in its own right. Our itineraries link Naxos and Amorgos self-guided or, in the west of the archipelago, Serifos, Sifnos and Milos. For a longer immersion, the grand guided tour from Andros to Amorgos makes up fourteen days across five islands. Crossings are booked in advance, with no logistics for you to handle.

What pace should I expect on these walks?

You walk at your own pace, without constraint. The days are composed à la carte, from a ridge path facing the open sea to a stroll from one taverna to the next, with almost always a turquoise cove for the swimming stop. The paved kalderimia, inherited from centuries past, are best taken quietly in the morning, before the heat. Nothing is rushed: here, the pleasure of light and flavours matters more than distance.