In this sailing guide, we will discuss sailing itineraries for the Cyclades. If you are chartering a boat to visit the Cyclades, you will probably do so from Syros Finikas, Alimos Athens, or Lavrio. 

Northern Cyclades Sailing Itinerary

Andros

The northernmost island of the Cyclades and quite different as it is green, wooded and cultivated. It is one of the largest islands of the group and mountainous throughout. Andros is the birthplace of many shipping families and is not dependent on tourism. Sariza, an inland village, bottles the famous Sariza mineral water, which is exported worldwide. 

For the sailor, the harbor of Gavrio offers the best anchorage on Andros, as it is a deep natural harbor well protected from the prevailing north winds, although there are gusts sweeping into the bay when the mealtime is strong. Caution should be exercised when entering the bay from S as there are two reefs SE of the bay. The most popular place on Andros, Batsi, is a smaller harbor approximately 3 miles SE of Gavrio sheltered from the Meltemi.

Tinos

Greek Orthodoxy’s most sacred island with the famous monastery of the Madonna of Tinos, honored on the 15th of August each year by pilgrims from all over Greece hoping for a glimpse of the icon or a token of its miraculous powers for curing the ill and the misfortunate. 

Beautiful uncrowded beaches, valleys rich in vegetation, and small villages considered rare examples of popular Greek architecture, with pigeon towers and white churches with blue domes and stone fences running through the whole island up onto steep rocky cliffs and down to calm blue bays.

Syros

Ermoupolis, the main port, is the capital of Cyclades and has a long tradition in shipping. To this day, it is one of the largest commercial ports in Greece. Classic buildings, old mansions, small houses painted red, pink or ochre, rest high up on the hills and sweep down to the port, resembling Europe of the 18th-19th century. 

Upper Syros is built on San Georgi hill, a medieval part of the island inhabited by 2000 Roman Catholics. Here you will see the famous Capucine monastery built in 1635 and the Jesuit monastery built-in 1744. Syros is blessed with many beautiful bays with sandy beaches and crystal clear waters, amongst them Megas Yialos, Phoinikas (yachtsmen’s favorite anchorage), and Galissa to the south, and Delfini, Aetos and Grammata NW.

Mykonos

This island needs no introduction as it is famous throughout the world. Arid and windblown, but sparkling with whitewashed clusters of houses, churches, and windmills overlooking golden beaches and glittering seas, Mykonos will enchant you. It will dazzle you with its endless cosmopolitan nightlife and visiting VIPs, its elegant shops and haute couture establishments. 

She’ll calm you and lull you on a golden beach bathed in bright sunshine and make a friend of you when her islanders smile at you, offering a simple fishmeal and ouzo at a little taverna by the sea. A tip to fellow sailors: avoid Mykonos harbor, prefer to anchor in Ornos Bay (it is approximately a mile to Mykonos town), or Plati Yalos immediately E of Ornos.

Delos

The heart of the Cyclades, with a history of 4500 years, Delos is perhaps the most important archaeological site, as the whole island was a religious sanctuary with homage paid to her by ancient civilizations who built temples and brought treasures for Apollo. Uninhabited since the fall of the ancient empires, it is alive with the echo of ancient life rising from marble ruins. 

For today’s pilgrim, Delos can be visited by sailing boat, but we strongly advise you to take the caique from Mykonos, leaving daily for Delos, as the waters leading to the hidden ancient port of Delos are full of shoals. Delos may be visited only from sunrise till sunset. When the sun sets over the island, it returns to the silence of its past glory…

Western Cyclades Sailing Itinerary

Kea (Tzia)

Although closest to Attica, Kea (or Tzia) is off the beaten track for most land tourists and will delight you with picturesque fishing villages, the inland town, and beaches for all tastes. The deep bay of Agios Nicolaos embraces the ferry port of Livadhi to the S, and Vourkari NE, which is the favorite yacht anchorage. 

Vourkari is renowned for its fish tavernas, and from there, you can visit the mountainous Chora (or main town), and the famous lion carved out of a rock face, a remnant of Keas ancient glory. Kea has many bays worth visiting. Koundouros (or Kavia Bay) approximately 5 miles S of Vourkari, is a favourite stop for a swim, protected from the N winds, although caution should be taken when entering because of the shoal extending from the N side of the entrance. Polais bay on the SE side of the island offers the visitor the added excitement of exploring the ruins of the ancient city.

Caution! Do not attempt to enter Polais Bay at night. The narrow passage between the shallows, although easily detected in daylight, tells another story at night…

Kythnos

An island bleached by the sun, washed by the sea and blown by the wind, Kythnos is a place to feel very close to nature. From the port of Merichas, at a distance of 7km, one can visit the main town of Chora, where there are many archaeological sites and Byzantine churches. On stone pavements and patios, local artists have painted flowers, fish, and sailing boats with lime. 

Narrow streets winding through the town with arches bowing over them, whitewashed houses, and windmills make Chora a beautiful town true to the Cyclades tradition of unique architecture. For the sailor, crowded Merichas is a trial. For those who prefer peace, we suggest anchoring in one of the twin bays of Fikiada and Apokriosis just a mile N of Merichas. 

The little port of Loutra on the NE side of the island is another favourite yacht anchorage. The hot mineral springs of Looter run to this day, while the village itself welcomes the yachtsman as a guest of honor.

Serifos

According to mythology, Serifos is the petrified Medusa killed by Perseus. It is a mountainous isle with the main town of Chora built on a hill overlooking the closed Livadi bay, where you should moor. Chora is one of the most beautiful towns in the Cyclades, and the view down to Livadi bay is overwhelming. 

Livadi is usually full of yachts as it offers fuel and water delivered on the quay, good provisioning, and excellent tavernas. A pleasant picture to the eye with green valleys and iron mines alternating with sandy beaches and blue bays ( don’t forget to stop for a swim at Koutalas Bay on the South). Serifos is a must.

Sifnos

Naturally protected by steep rocky slopes surrounding it, allowing small bays to form between them, Sifnos has a wild beauty of its own to be discovered only by the lucky ones who sail there, as most bays are not linked by road. 

Sifnos has 400 churches and 20 monasteries while at Kastro, there is an archaeological site where you can see remains dating as far back as the geometric period of the 9th century BC. The bays of Sifnos are renowned for their beauty, and the photo on the right of Panagia Chrysopigi is the entrance to one of the most famous.

Middle Cyclades Sailing Itinerary

Paros

Surrounded by beautiful sandy beaches, Paros is quite green in parts and famous for its rich markets. Of great archaeological interest, the island blossomed for 7 centuries beginning in 1000 BC, and most ancient temples were built of Paros marble. The ancient quarries can still be seen at Marpissa, together with a number of unexplored caves. 

Paroikia, the main port is a typical Cyclades town with whitewashed houses spread along the waterfront, interlaced by narrow cobble streets, arches and balconies overflowing with flowers, while a fleet of fishing boats fill the harbor. Naoussa is one of the most picturesque fishing villages in the Aegean, surrounded by castle walls: a favorite stopover when sailing around the island.

Antiparos

The island of Antiparos is separated from Paros by a narrow channel with many shallows, which should only be sailed through by day, preferably in calm weather when the reefs are easily visible. Deep draught yachts should not attempt the channel passage. The village of Antiparos is delightful, and the small harbor offers good shelter from the prevailing northerly winds (Meltemi). South of Antiparos, the uninhabited island of Despotiko, has a large sandy bay on the S side, also protected from the Meltemi wind.

Naxos

The largest island of the Cyclades it is made up of rural villages in the interior, lined with olive groves, vineyards and lemon groves sprouting from the rich earth, as she was the chosen island of the god Dionysos who blessed her with great fertility and excellent wine. Naxos is rich in archaeological and Byzantine monuments, and we suggest a prolonged tour of this island as it is so different from the others.

Caution! If you decide to dock in Naxos harbor, beware of the wake caused by passenger ferries (in fact, beware of them in any Cyclades port).

Little Cyclades

South of Naxos lies a group of small islands famous amongst sailors. Beginning with Iraklia, a small island just 3 miles South of Naxos, most yachtsmen prefer to spend the night in charming Skhinoussa, just a mile North-East of Iraklia, where the almost landlocked bay of Myrsini offers good shelter from the Meltemi. 

Another mile North-East you come across two islands known as Koufonisia. Kato (Lower) Koufonisi is not inhabited, while Ano (Upper) Koufonisi has a small fishing port and to the North-East one of the most spectacular beaches of the Aegean, about 1 mile from the port, recognized by a sole palm tree on the sandy beach. Anchor in 3-5m of sandy bottom. Beware of the surfacing rock! Dhonoussa, a very windblown island just 9 miles E of Naxos, is truly off the beaten track, and for the fortunate ones who are able to sail there (winds permitting) this unspoiled island has many attractions to explore. 

You can set anchor either in Dhonoussa harbor (S) where there is a little village, or immediately East at Dendro Bay or at Roussa Bay on the E – NE coast, which offers shelter from the north winds sheltered by the little island of Trigono.

Amorgos

A mountainous island with spectacular cliffs dropping straight down to the sea, most notably on the NE and on the S coast. The main port is Katapola at the S end of the deep bay crowned by the white houses and windmills of the town (Chora)on the hill. From Chora, you can visit the famous monastery of Panagia Hozoviotissa, half-tucked into a cliff – half hanging sheer over the sea. 

There are quite a few anchorages on the W side of Amorgos, namely from N to S Agia Anna (open to the W-NW), Kalotiri Bay (on the SE side of Nikouria Island), Akrotiri Bay(open to the NE) and Kolofana Bay (S of Gramvousa island).

Caution! Kakoperato Strait between the island of Nikouria and Amorgos needs extreme care when passing through, and although it can be done, many boats have been seen stuck in the channel.

Southern Cyclades Sailing Itinerary

Milos

The island of Aphrodite (Venus), where visitors will meet the most ancient of all Aegean civilizations beginning about 5000 years before the first Hellenic and reaching its peak during the Bronze Age. 

Magnificent beaches (particularly on the S side), a healthy climate and beautiful landscape enriched with green and mineral waters, give you a feeling of being reborn. At Plaka, the main town built on a plateau 200 m above the sea, the Cycladic architecture is fascinating. It is an open “window”; to the sea. A visit to the archaeological museum will give you an insight into this ancient civilization and also a chance to see a replica of the famous statue of Venus de Milo found on the island in 1820.

The statue was taken out of Greece, and one can see it today at the Louvre Museum in Paris. At Klima, the famous catacombs of Milos, the only early Christian monument in Greece, which, together with the catacombs in Rome, are considered the most important of early Christian times, can be seen and it is near here that the famous statue of Venus was found.

Ios

The most popular of the Cyclades among the young, it sings by night alive with youngsters from all over the world, dancing to disco rhythms rising from the numerous bars and discos found along the narrow cobbled streets of Chora on the mountain or at Skala, the waterfront at the end of a very deep bay, where you can moor and be protected from all winds.

Ios boasts some of the most beautiful sandy beaches found anywhere, like Milopotas and Manganari. Take a boat to visit neighboring Santorini, the giant volcano island.

Santorini (Thera)

The main island of Thera is shaped like a new moon surrounding the rim of the crater, which sunk a thousand meters under the sea in the eruption of 1500BC. It is believed that the biblical sinking of Thera hides the secret of lost Atlantis. The island of Therasia is also part of the crater’s rim, whilst an accumulation of lava and ash forms the islets of Kameni and Nea Kameni. The dazzling white town of Thera (Fira) built on a cliff dropping sheer into the sea from 700ft, is a devastating sight, as donkeys carry you up the 580 steps to the top of the cliff.

Caution! You cannot drop anchor in Santorini (Skala Thiras) as it is very deep. There is a buoy about 100m from the quay. Tie a line and moor stern to the quay. It is difficult to leave when you choose as other yachts arriving after you will hem you in. That’s why we suggest you moor in Ios and take a caique over to Santorini.

On the other side, black sand beaches and vineyards present a more placid nature of the largest known active volcano in the world. Near Akrotiri are the excavated ruins of a whole Minoan town, which was destroyed during the eruption of 1500BC. They are considered one of the most important archaeological discoveries in the world.