Things to see & do in the Cyclades
So called because they form a circle around the sacred island of Delos, the Cyclades are the sun-drenched stuff of island hopping fantasies. Scattered with sugar-cube houses, blue-domed churches and top notch archeological sites, they look as if they are straight off a film set. What makes them even more enchanting is their variety. You’ll find laid-back isles where traditions hold strong, sophisticated idylls primed for romance and quiet corners away from the restaurant strips on the busier islands. Most of them can be hiked, biked, kayaked or snorkelled. Sure, some areas get busy during the peak summer season, but there are plenty of remote, off radar spots where you can escape the crowds and have the beach to yourself.
To get around you can ferry-hop or join a small group cruising or sailing tour travelling by private boat in a group of up to 16 like-minded travellers, with expert guides to help make sure things run smoothly along the way. Either way you’re living the island dream.
Cyclades walking holidays in Greece
A gently active holiday in the Cyclades
From
£1875 to £2195
8 days
inc UK flights
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From
£785 to £872
7 days
ex flights
Naxos and the small Cyclades walking holiday, Greece
Walk and discover Naxos and the unspoilt Small Cyclades
From
£645 to £1025
10 days
ex flights
Cyclades walking holiday, Greece
Walk ancient paths and enjoy stunning Cycladic sceneries
From
£645 to £717
7 days
ex flights
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From
£1230 to £1540
8 days
ex flights
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From
£1230 to £1385
8 days
ex flights
Where to go
Naxos is the biggest island in the Cyclades and home to the group’s highest peak, the 1,004m high Mount Zas. The island is the fabled home of the ancient Minoan princess Ariadne, with the Old Town overlooked by a hilltop castle and scattered with 16th century Venetian homes. If you’re going on a sailing odyssey around the islands you’ll likely start here, and it’s also the main transport hub for the islands.Then there’s Mykonos, favourite of hedonists and high-flyers and home to fine dining restaurants, posh hotels, a yacht-stuffed marina and a thriving gay scene. It also has its share of quiet coves and pretty countryside to explore. The white villages and iconic sunsets of Santorini have graced a thousand magazine spreads, but it’s also a walker’s paradise with plenty of dramatic trails. On mountainous Amorgos, walking paths lead to ancient churches and unspoiled bay, while on Paros, a network of Byzantine footpaths take you to traditional villages. Less visited than the others are the tiny islands of the Lesser Cyclades and the Western Cyclades. Hike and hop these islands to experience something special on each one, including the Cyclades’ largest cave on Iraklia.
Getting active
Strapping on your boots and hitting the trails on a walking tour is the best way to get to know the Cyclades Islands. Beyond the beaches, trails pass through hills covered in wild herbs, through pretty villages and Venetian towns, past Byzantine chapels and ruined temples, and on to tiny tavernas where the food is as spectacular as the sweeping views. Leisurely is the world of choice when it comes to walking breaks around these parts. Distances are moderate, with between two and five hours walking a day, the terrain is easily negotiated and walks are interspersed with swimming, picnicking, sampling local wine and discovering ancient sites.You could choose to spend a week getting to know a single island in depth or spend up to two weeks sailing from island to island by yacht or ferry, exploring new paths on every isle. The majority of our walking holidays in the Cyclades are run as small group breaks, with a maximum of 16 people taking part. You could also choose one of our tailor made walking tours. These often include a local guide, but provide greater flexibility on how long you stay and where you walk. Either option will introduce you to locally run hotels and restaurants, so you can be sure your money is going into local hands.
If you want something a little different, you could always opt for a cycling tour. You’ll spend your days cruising from island to island and exploring historic sites, towns and villages by bike, at a relaxed and enjoyable pace. Either guided or self guided, these are suitable for the moderately fit, and always build in plenty of time for swimming, resting and sightseeing.
Our top trip
Cyclades walking holidays in Greece
A gently active holiday in the Cyclades
From
£1875 to £2195
8 days
inc UK flights
Small group travel:
2024: 31 Mar, 14 Apr, 5 May, 19 May, 2 Jun, 29 Sep, 6 Oct, 13 Oct, 20 Oct, 27 Oct
2025: 23 Mar, 30 Mar, 13 Apr, 4 May, 18 May, 1 Jun, 15 Jun, 14 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 27 Oct
2024: 31 Mar, 14 Apr, 5 May, 19 May, 2 Jun, 29 Sep, 6 Oct, 13 Oct, 20 Oct, 27 Oct
2025: 23 Mar, 30 Mar, 13 Apr, 4 May, 18 May, 1 Jun, 15 Jun, 14 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 27 Oct
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Cruising
Given the beauty and diversity of the archipelago, with over 200 islands to choose from, it’s not surprising that people are reluctant to stick to just one. Luckily there’s a generous handful of sailing and small ship cruising holidays to get you from port to port. 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.
You could glide between the islands on a small yacht sleeping just eight passengers, where everyone mucks in to help it sail; or go bigger and fancier (though not floating hotel big) and island hop on an elegant 49 sleeper motor yacht equipped with sunbeds, a Jacuzzi and a bar.
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