Walking holidays in the Cyclades
trails of light between white villages and turquoise sea
The scent of wild thyme greets you from the very first steps. Ahead, a kalderimi of pale stone winds between low walls, whitewashed chapels and caper bushes towards a village that could be a postcard, were it not for the plate of mezze waiting for you on the terrace. Walking in the Cyclades is lived like this: at an easy pace, feet on stone paths centuries old, eyes on the deep blue of the Aegean. From Sifnos the gourmet to Amorgos the wild, our walking holidays in the Cyclades open the doors to an archipelago you truly discover only on foot.
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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.