Walking in the Cyclades

The Cyclades, an archipelago of over 200 islands lying southeast of the Greek mainland, pull in their share of peak season tourists, eager for a week on the beach, but there is so much more to enjoy here when you step beyond – literally – the coast. Walking breaks take you island hopping and exploring, with two feet transporting you to caldera rims with long views over the Aegean, to buried Minoan cities and ancient marble quarries, through olive groves, vineyards and fields of wildflowers and along historic routes to Byzantine chapels or ruined temples.
Explore a single island in depth in the course of a week’s walking, sail between the Cyclades’ lesser visited gems on a small yacht, or relax with the locals as you chug between the main islands of Paros, Naxos and Santorini on a ferry, before stepping out again to make new discoveries. However and wherever you walk in the Cyclades, you’ll discover Aegean views to die for at every stop, remote beaches at the end of every trail and waterside tavernas welcoming you with fresh local food at the end of each day.
Where to walk in the Cyclades

Where to walk in the Cyclades

Some small group walking breaks focus on the larger Cyclades – Naxos, Santorini and Paros. These three islands are home to a wealth of walking trails, beautiful white painted villages, historic sites, pretty beaches and wonderful cafes and restaurants. Follow the Tragea Valley through the interior of Naxos, walk the 10km Cliff Trail on Santorini enjoying neverending views of the Aegean, or stride out on the Old Byzantine path that runs from the village of Lefkes all the way to the east coast of Paros. There are ancient sites to enjoy, too, and the ancient Minoan settlement of Akrotiri on Santorini is a standout highlight. This Minoan Bronze Age settlement, a sort of prehistoric Pompeii of the Aegean, was buried under lava in 1627 BC.
Other walking holidays move between the Small Cyclades and the lesser visited islands of the archipelago, such as Amorgos, which boasts an ancient circular path; Iraklia with a population of just 80; and Koufonisi, famed for its particularly clear, turquoise waters. This is a chance to experience an authentic side of the Cyclades; to eat in tiny local tavernas where produce from the owner’s garden is always on the menu, and the fish freshly caught just hours ago. You’ll receive a warm welcome in these untouristy islands, too, and any money you spend will benefit these small, more remote communities.
style & fitness

Walking style & fitness

Unlike a trekking holiday that follows a demanding point to point route, with hours of hiking each day, a walking holiday in the Cyclades is more about exploration on foot. Walks range from leisurely to moderate, but are never graded as challenging or tough and don’t involve altitude. Generally, an average level of fitness is adequate – we’re not talking extreme sports here.
You’ll typically walk every day, but walks are interspersed with swimming, picnic and café stops, sampling wine at a local winery and discovering ancient sites. Every itinerary varies, but a leisurely walking holiday will include walks of manageable distances, some as short as 2km, others 10km. Expect walking times of between two and five hours including lunch breaks and typically ascents of no more than 500m. On most small group holidays, and certainly on a tailor made trip, remember that walks are entirely optional, so if you prefer to relax on the beach or read in a cafe one day, you can.
The majority of walking holidays in the Cyclades are run as small group breaks, with a maximum of 16 people. These blend guided walks with cultural visits, superb food in local tavernas and down time. You can also opt for a self guided break, during which you’ll follow a well designed itinerary. You’ll have local support and an information package, which details the routes but also gives facts on cultural, archaeological and natural sites of interests, as well as the best tavernas, cafes and places to picnic. Tailor made walking holidays are also an option. These often include a local guide, but provide greater flexibility on how long you stay and where you walk.
Walking holidays in the Cyclades tend to be a week long, but four-day trips, which focus on a single island such as Santorini, are a great short break option. Many walking holidays also have a flexible itinerary, which can be extended or trimmed by a few days, depending on what time you have available.
In terms of kit, you’ll need walking shoes and perhaps poles, especially if your holiday includes walks on steep or rocky routes. Bring layers, for peeling off or putting on, as although most walking holidays in the Cyclades take place outside peak season, you will still experience daytime heat and evening chills.

Our top Cyclades Holiday

Cyclades walking holidays in Greece

Cyclades walking holidays in Greece

A gently active holiday in the Cyclades

From £1899 to £2199 8 days inc UK flights
Small group travel:
2023: 2 Apr, 16 Apr, 7 May, 14 May, 4 Jun, 18 Jun, 3 Sep, 17 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct
2024: 17 Mar, 31 Mar, 14 Apr, 5 May, 12 May, 2 Jun, 16 Jun, 1 Sep, 15 Sep, 29 Sep, 6 Oct, 13 Oct, 20 Oct
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Other activities

Combine with other activities

Sailing and walking combine perfectly in the Cyclades, with a small yacht that takes just six passengers gliding between islands. Unlike public ferries, which only travel between the larger islands, a sailing yacht can get you to the small and even uninhabited islands of the Cyclades archipelago, where you can walk to discover deserted villages, Venetian settlements and empty beaches.
On Iraklia, for instance, there are several walking trails, but a beautiful option is to head out from the town of Panayia to the ancient cave of St John, the largest cave in the Cyclades, famous for its dramatic stalactites. You’ll reach a high point where you can drink in the sunset, before dropping back down to Panayia for dinner at a taverna which also doubles as the village bakery. On a combined sailing and walking break you can also visit seriously off-the-beaten-track islands such as Kato Koufonisi, where the taverna is owned by the only family resident here.

When to go walking in the Cyclades

Walking holidays in the Cyclades are best taken from April through to the end of October, but trips don’t generally run in July and August when the weather is too hot for walking.
In April, life here is relaxed, before the peak tourist months arrive, and it’s often cheaper to travel now. The sea is a bit on the fresh side, so swimming is bracing or best avoided, but the landscape is green, with lots of flowers bursting into bloom and looking lovely until mid June. Temperatures are pleasant, too, and if you come over Easter you can experience traditional feasts and celebrations going on all over the islands. From September until the end of November temperatures drop off after the heat of July and August, and the walking becomes great again in the Cyclades. The first few showers refresh the landscape and autumn crocus appear, plus the sea is warm for swimming after a summer of sunshine. The grape and olive harvests also happen now, with lots of local festivities to enjoy.
Written by Joanna Simmons
Photo credits: [Page banner: Chris Brooks] [Santorini hike: Ken Curtis] [Akrotiri : **AB**] [Amorgos: Hector Champipis] [Woman hiking in Santorini: Ana Raquel S. Hernandes] [Local wine seller at the becah: Bryce Edwards] [Walking down the hill: Chris Brooks] [Walking back from Homer's tomb: Chris Brooks] [Sail and swim: ristok] [Local taverna: Chris Brooks] [Daisies in bloom: Klearchos Kapoutsis]