How to spend two weeks sailing around the Cyclades

The Cyclades archipelago represents the pinnacle of rugged Mediterranean beauty, with whitewashed villages, empty beaches and a burgeoning food scene. And if you can’t choose which one to visit, why not charter a boat and sail between several?

By Greek National Tourism Organisation
Published 8 Sept 2020, 15:16 BST
Koufonisia is a haven of blissfully deserted beaches and solitary tavernas selling mouthwatering local fare.

Koufonisia is a haven of blissfully deserted beaches and solitary tavernas selling mouthwatering local fare.

Photograph by Getty Images

For crowd-free islands, Naxos and the Minor Cyclades have been fiercely guarded by those in the know. Slowly though, travellers are catching onto their electric blue seas, powder-soft sands, scented hiking trails and sleepy villages. Hire a boat and sail between them — before the secret’s well and truly out.

Days one-four: Naxos

Charter a boat in Mykonos, leaving the busy hotspot behind for the first sail of your journey. It’s a salty, windblown crossing to Naxos, covering 22 nautical miles, and you’ll likely arrive at Chora’s port in the balmy evening heat. Spend the next day meandering around its jumble of whitewashed houses, stone alleyways and churches, lorded over by the castle of Hora whose surrounding mansions are still inhabited by Catholics of Venetian descent. Be sure to try the local citron liqueur, kitron, and pay a visit to the Archaeological Museum with its wonderfully preserved collection of Cycladic figurines, as well as the temple of Apollo, a huge marble gate built in 530 BC. Set your alarm early the following morning and get a bus to Aria Spring for a three-mile-round hike to the tip of Mount Zas — the highest point in the Cyclades — along sage-scented trails, and through orchards, olive groves and vineyards. At its summit, you can gaze down on Naxos, with the other islands no more than pinpricks in the Aegean. Back down at sea level, and before heading to the coast, make a side trip to the village of Apeiranthos. This is a place untouched by the passage of time, rising like a fortress from the foothills of Fanari mountain. Admire the architecture — unique among Cyclades villages — over a plate of local cheeses; the graviera, made of cow, sheep and goat’s milk, is the most famous. Next up, head to the coast. Plaka beach, just south of Chora, has water that glistens a thousand shades of blue, and plenty of beachside tavernas to enjoy and beer and plate of freshly caught fish.
Need to know: Mykonos has boat hire options for every type of sailor, from bareboat to skippered to fully crewed yacht chartering. Shop around before you choose which operator to go with.  

The largest of the Cyclades, Naxos, is home to secluded mountain villages, isolated beaches and ancient treasures. 

Photograph by Getty Images

Days five-six: Iraklia

As you depart Naxos and sail down its south coast, drop anchor at near-empty Kalandos Bay, where you’ll catch the smoky scent of barbecued fish spiralling from a single beachside shack. Next up, head to Iraklia, an island with well-kept walking trails. Starting from the port, follow signs along a dusty track to the Cave of the Sacred Icon of Agios Giannis, a two-hour hike with incredible views and where, at its end, you’ll find a series of caves whose walls ripple with stalagmites and stalactites. Turn back to the port and flop on the beach of Agios Georgios for a snooze under the pines, before strolling along its sun-drenched three-mile shoreline. Turtles are a common sight in the waters around Iraklia, especially just up the coast on Livadi Beach. Plus, if you find yourself in Alimia Bay on the island’s southwestern tip, the wreck of a sunken Second World War German plane lies just offshore. Slip on a snorkel and swim directly from the beach to float above its foliage-covered shell.
Need to know: The port of Agios Giorgios sits at the head of a fjord-like inlet, and only has room for between three and five yachts, so arrive early to secure a spot.

Slow, sleepy Iraklia welcomes lots of boats to its sheltered harbour in the summer months. 

Photograph by Getty Images

Days seven-eight: Schinoussa

Just four nautical miles north of Iraklia, your next stop is the tiny island of Schinoussa in the centre of the Minor Cyclades. Berth in Mersini Bay, once a notorious pirate port, and have a dip before walking its perimeter. You can hike the whole circumference in a couple of hours, but take it slow, pausing to swim in the empty coves dotted around the island, as well as the tiny village of Messaria, with its wonderful array of family-run vineyards. Mersini draws yachties from all over to its sheltered cove in order to gather supplies from the little village of Chora. Stock up with a picnic of fresh figs, stuffed tomatoes and vine leaves and take a break from the helm, boarding one of the daily boat trips to the nearby islets of Ofidoussa, Agrilos and Aspronisi.
Need to know: Mersini’s bay is deep and narrow — the inlet is almost 2,000ft long. Its entrance faces south, and it’s one of the safest anchorages in the Aegean.

Schinoussa's undulating hills make it ideal for hiking, with views stretching out across the Aegean. 


Photograph by Getty Images

Days nine-eleven: Koufonisia

These islands – around five miles east from Schinoussa — are about as remote as it gets. There’s no nightlife to speak of, and certainly no high-end hotels; it’s a haven of blissfully deserted beaches and solitary tavernas selling mouthwatering local fare. Anchor on Pano, the main island with its tiny, blue-and-white fishing village, and wander down narrow pathways where bougainvillea bursts from gardens and the smell of pine lingers in the air, before sitting down to olives and ouzo at a harbourside restaurant. Spend the following morning on a hired bike, pedalling two miles to Pori Beach, where you’ll find a handful of windsurfers testing their mettle on the waves, but on route keep an eye out for an enormous natural pool half hidden in the rock; the perfect place for a halfway dip. Then, it's onwards to Fanos about a mile to the east, or alternatively, if you’re craving complete solitude, hop on one of the regular boats from town to the uninhabited Kato Koufonisi, where you can snorkel and dive around sea caves carved into rocky outcrops. Finally, there’s tiny Keros, a speck of an island currently off-limits to visitors due to ongoing archaeological research, but one to admire as you sail away from Koufonisi and towards your final island: Donousa.
Need to know: Pano, Kato and Keros make up Koufonisia, but out of the trio, Pano is the only inhabited island.

Koufonisia is picture perfect, with classical blue and white houses and traditional waterfront tavernas. 


Photograph by Getty Images

Days twelve-fourteen: Donousa

Slow-paced Donousa is a closely guarded secret for travellers determined to sail the extra mile, reached via a slightly blustery northeastern crossing. Drop anchor in the main hub of Stavros and stroll for 15 minutes down the coast to Kendros beach, a popular stretch of sand curving around a sheltered bay. Alternatively, for a quieter beach hike an hour to Livadi, a little further along the east coast, before wandering inland to the village of Mersini, where diners linger over baked feta and sticky honey pastries, sand still between their toes. This dinky isle is also striped with hiking trails winding through timeless villages, but if the pull of the sea is too great, head towards the island’s sea caves: Spiliá Tíchou with its dripping stalactites, or Fokospiliá where you might be lucky enough to spot seals lazing in the sun.
Need to know: Sailing to Donousa can be a challenging route with strong winds, especially around midday. Try and ensure you travel in the mornings when the seas are calmer. From Donousa it's 30 nautical miles back to Naxos, so leave early and allow for a full day of sailing, keeping your eyes peeled for dolphins and seals.


Donousa is the most far-flung of the Cyclades, with a prominent north-west cape.

Photograph by Getty Images


Getting there and around
Several airlines fly from London, Birmingham and Manchester to Athens, where connecting flights will take you on to Naxos. Once there, there are a multitude of sailing companies to choose from.

When to go
Sailing around Cyclades islands is best experienced in the summer, when temperatures average 35C and seas are normally placid. 

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