Discover the Cyclades by sailboat: 10 top destinations for setting sail

Un voilier dans les cyclades

If you dream of discovering the wonderful Cycladic islands by sailboat, follow our top 10 destinations for sailing in the heart of the Aegean Sea.

From April to October, sailboats ply the Aegean between the magnificent Greek islands of the Cyclades. Sailing in the Cyclades is a relaxing moment in an idyllic setting. You’ll enjoy a unique experience, making the most of every island.

Because the Cyclades are unique in that, despite their proximity, the 24 inhabited islands of the archipelago are all unique. You can go from ochre to green, from flat mountains to vegetation. And the best part is seeing the whole from the sea, as only sailing can offer.

As long as you know how to protect yourself from the local wind, the Meltem, which can chop up the sea and shake the waves from June to September! Find out more about our 10 top destinations for sailing in the Greek islands of the Cyclades!

Head for Paros, in the heart of the Cyclades archipelago

voilier dans le port de Paros, dans les Cyclades

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On a sailing holiday in the Cyclades, you’ll love your stopover in Paros, in the center of the Cyclades. This island is more popular for the beauty of its beaches than for its interior. But the land is well worth the detour, with its wild scrubland dotted with monasteries and footpaths. And let’s not forget the beautiful vineyards, where you can sample fine local wines.

If you’re visiting the island by sailboat, you’ll want to anchor in the northeast of the island, in the Bay of Naoussa. In summer, it can be very busy, as it’s also one of the trendiest spots on the island – it’s often compared to Saint-Tropez. The advantage of the bay is that it provides shelter from the wind if it picks up strongly.

Out of season, Naoussa suddenly takes on a calmer, more peaceful aspect. You can also choose to sail between Paros and Antiparos, where a pleasant channel allows you to sail between the two islands. For boat hire, prefer the main port of Perikia, but you can also find an option in Pounda, the port opposite Antiparos.

A calm or festive break on Mykonos

voiliers dans le port de Mykonos, dans les Cyclades

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Mykonos needs no introduction for its festive and trendy character. But what you may not know is that the island still has some quieter spots that have been left behind by bling tourism. Perhaps you’d like to take a boat trip to a peaceful cove.

Let’s face it, Mykonos is best visited out of season. In the height of summer, even the quietest coves can be jammed with anchored yachts. Off-season, on the other hand, you’ll appreciate the peace and quiet! Mykonos will charm you with the beauty of its beaches and the relief of its contours.

And with your sailboat, you’re just a short hop away from the archaeological site of Delos Island, an ancient Greek sanctuary. If you’d like to hire a boat, you’re spoilt for choice. From the new port of Tourlos to Elia, every village on the southwest coast has one or more charter companies offering services by the day or week, with or without skipper.

Santorini, an essential stopover

Bateaux à voile au large de Santorin au coucher du soleil

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Sailing off Santorini on a sailboat – what a sweet dream! Unfortunately, you won’t be the only one to choose this option. We’d like to warn you right away: make sure you choose the right season to visit Santorini. Without a reservation in high season, it can be a complex experience. If you’re arriving by sailboat from outside the island, be sure to plan ahead, as all anchorages and berths are overbooked.

Between September and June is the best time, as you can take advantage of the dead bodies that the locals leave behind for nine months. But in summer… It’s best to come to Santorini out of season. You can get close to the famous Red Beach in the south of the island, or nestle peacefully at the foot of the charming village of Oia in the north.

You’ll also appreciate the Kameni islets, the result of one of the last eruptions of the Santorini volcano. The red slopes emerging from the turquoise sea are just breathtaking. You can hire skippered sailing boats directly from Santorini. You’ll find private charter agencies in Vlychada, Perissa and at the old port of Fira.

Passing through the central island of Naxos

Voiliers dans les cyclades

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A stone’s throw from Paros, Naxos acts as a big sister due to its size. It’s also a hub of maritime traffic in the Cyclades, as many ferries stop here, particularly in high season. So be on your guard when sailing between the Greek islands in summer.

Apart from this relative constraint, you’ll appreciate the unique character of Naxos, a verdant island that’s home to the highest peak in the Cyclades. Mount Zeus – the name says it all! – rises to an altitude of 1,002m and is an immediate eye-catcher. If you’re sailing, you’ll have a good view of it as you pass to the east of Naxos, which is also the wildest part of the island.

Boat rentals are available in the opposite direction, mainly at the port of Naxos. You can also find boat rentals at Agia Anna, further down the west coast. And if you like water sports, you’ve come to the right place. Around Naxos, you’ll find plenty of windsurfers and kiteboarders having a great time off the coast.

Milos, the perfect island to start your cruise

Voilier dans une crique de Milos, dans les Cyclades

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Some say that Milos is better visited by boat than by road. An interesting argument if you hesitate to come to Milos by sailboat! In fact, the volcanic island is magnified by its coastline. That’s why it’s perhaps best appreciated from the sea. The Sikia cave and the white cliffs of Kleftiko, for example, are natural wonders.

You can circumnavigate the island at a slow pace, carried along by the freshness of the open sea. And when you feel like it, drop anchor and dive into an abandoned cove! Milos is renowned for its sailboat cruises, so there’s no shortage of boat rental companies and skippers. All around the island, the main villages each have one or more private charter companies you can turn to.

A stopover in Ios on a Greek sailing tour

Ios, Grèce Un voilier dérive par des parasols sur les rives d'Ios, Grèce

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Ios is not the best-known of the Cycladic islands. It’s said to be very festive and noisy, bringing together English-speaking youth from all over the world ready to battle it out day and night with resounding music.

While this is true for Chora, the capital, the rest of the island remains calm and serene, as is island life in the Cyclades. With your sailboat, choose the quiet places if you want to sail in peace and quiet. If you’re stopping off in Ios to enjoy a good binge and a bit of nightlife during your sailboat cruise, then converge on Chora!

When it comes to quiet spots, you’re spoilt for choice. The sheltered beaches to the south, such as Tris Ekklisies and Magganari, come to mind. To the northeast, head for Agia Theodoti, a beach less accessible by car: of course, having a sailboat gives you a great advantage for enjoying the area, even in high season.

Enjoy a stopover on Amorgos

Voilier sur un coucher de soleil à Amorgos, dans les Cyclades

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It’s unlikely that you’ll reach Amorgos via the east coast, so hurry around the island to see the grandeur of the Panagia Chozoviotissa monastery. Clinging to the side of a cliff, it dominates the Aegean Sea. You’ll see that there’s no shortage of clifftop scenery on Amorgos. Theisland is rocky, with few sandy beaches.

It’s also worth noting that the south is wilder and therefore more suitable for anchoring than the more touristy north. For example, Kalotaritissa beach is a good place to spend the night. Here you’ll find a shallow bay surrounded by rolling hills and scrubland: a true Greek bath. You can also land on Nikouria, the islet facing Amorgos.

Its crystal-clear water is a magical place for diving. It’s also an ideal shelter from the wind, thanks to its small bay. Beware, however, of the traffic in high season, whereas from September to June, you’re more than welcome! Boats can be hired from the island’s two main ports: Katapola in the south and Ormos Egialis in the north. In short, an ideal itinerary for cruising the Cyclades by sailboat.

To visit the Cyclades by sailboat, don’t miss Folegandros

Folegandros, un voilier navigue au large d'une ville

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We’ll start with the bad news and then move on to the good: in August, don’t even think about it, Folegandros is saturated. Here’s the good news! Folegandros by sailboat is a wonderful idea. Firstly, because the road network is limited, many places are more easily accessible by sea. Secondly, outside the famous month of August, theisland is very calm and has retained its authenticity.

If you’re looking for a place to sleep, consider the anchorage opposite the ferry dock at Latinaki beach. As traffic is limited outside the high season, you’ll be able to relax and take the road directly to Chora, a few kilometers further north. Alternatively, take advantage of the wild west coast, with its endless beaches just waiting for you!

Opt for Syros, the capital of the Cyclades

Voilier sur la baie de Finikas, près de Syros

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Syros is home to Ermoupoli, the capital of the Cyclades. Its role as an administrative center gives it a year-round existence and independence from tourism. Syros is therefore an ideal stopover on a sailing cruise in the Cyclades, especially as the northern beaches are inaccessible by car.

This guarantees a calm, zen-like experience, with coves just for you. Just think of Americanou Beach, where a sandy beach awaits you surrounded by small, bushy mountains. Even in July and August, Syros is not overwhelmed by mass tourism. A real luxury in the Cyclades!

This means you can get as close as possible to the southern beaches, which are more accessible from inland roads. This will allow you to disembark and explore this charming island, in particular Ano Syros and Ermoupoli, the nerve centers of Syros. Boats can be hired easily from the port of Ermoupoli, as well as from Kini to the east.

To get off the beaten track, head for Andros

Voilier dans la marina d'Andros

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Like Andros, Andros is not dependent on mass tourism. It’s even jealously guarded by Athenians who spend weekends there in their second homes. In Andros, you won’t find souvenir stores or a village with a waterfront full of restaurants, so you’re off the beaten tourist track.

The island is green and pleasant, benefiting from its freshwater resources. So you can make a stopover and venture out once your yacht is in port or at anchor. As far as sailing around Andros is concerned, it’s an absolute must! The island is one of the largest in the Cyclades archipelago and offers a wide variety of landscapes.

In the south-west, for example, Yalia beach lies at the foot of a brown striated mountain. Conversely, the north of the island is more green. Wherever you go, whatever the season: you’ll always find room to enjoy the tranquillity of Andros.

If you’re a sailing enthusiast, you’ll be able to set sail for the Cyclades thanks to all our recommendations. It’s hard to choose between all these islands, which invite you to let time flow by and let yourself go in the face of their beauty. So don’t hesitate to make several! Which ones tempt you most?