Sailing the Cyclades Islands

Mykonos and Paros

Day 1: Lavrio – Kea

Kea is the first island of the Cyclades and a good stop as the port is protected from the North winds. You can either moore on anchor in the bay or on the small dock. You can rent a car or take a taxi to explore the island or just relax in the bay, definitely try the tavernas by the dock.

Day 2: Kea – Syros

A long leg but worth it, if you are too tired you can go to the nice bay of Foinikas with the 2^nd largest settlement of the island or sail directly to the town of Ermoupolis which is also the capital of the Cyclades. This was an old Italian colony so you will also see different architecture in the old town than other Cyclades islands. The two hills in the centre of the town one with the Catholic church and community and the other with Orthodox church and community make this island quite unique.

Day 3: Syros Ermoupolis – Mykonos

Mykonos is the most famous Greek island and the most cosmopolitan. You must visit Little Venice, the Windmills and walk in the small streets of the town where the Cyclades architecture is at its best. Make sure that either after or before you arrive to go to the small island of Delos just opposite Mykonos. The island of Delos is one of the most important mythological, historical, and archaeological sites in Greece.

Day 4: Mykonos – Paros

The island of Paros which is one of the most famous Greek islands with the exquisite beaches and small villages. The village of Naousa is perfectly protected from the winds and has a very vibrant atmosphere during the summer months while also having very good tavernas.

Day 5: Paros – Syros Foinikas

Foinikas is a beautiful beach in the west of the Island, it is a popular destination due to its infrastructure featuring all comforts and conveniences such as an organized marina for the yachts and traditional fish taverns right by the sea.

Day 5: Syros Foinikas – Kithnos Loutra

At the small port of Loutra you can see the natural springs and baths while also relax in the small and picturesque marina. If you have time get a taxi and visit the main village of Kithnos which is inland and is very beautiful with its traditional Cyclades architecture and small streets.

Day 7: Kithnos Loutra – Lavrio

A sailing day and last chance to enjoy the Aegean sea before you return to Lavrio. Just before you arrive stop for a swim at Sounion Bay you anchor just under the temple of Poseidon and you are protected by the prevailing north winds.

Two Weeks to Santorini

Day 1: Athens – Sounion Bay

Sounion Bay is the perfect stop for the first day of sailing. You anchor just under the temple of Poseidon and you are protected by the prevailing north winds. Perfect setting to have dinner under the stars and the temple.

Day 2: Sounion Bay – Kithnos

Arrive at Kithnos island and the one of a kind Kolona bay (a strip of sand divides the bay into two). You can either stay all night at the bay on anchor (and visit the Taverna on the beach) or go to Merichas port which is just 1nm away for the night.

Day 3: Kithnos – Serifos

Serifos’ main village with white houses and blue windows is on a hill at the entrance of the main port which makes it very picturesque when sailing in and a must see visit in the evening to see the sunset.

Day 4: Serifos – Sifnos

Visit Sifnos as it is famous for its cuisine, the bay in Vathi is very well protected and can good place to spend the night.

Day 5: Sifnos – Kimolos

A short run to Kimolos island and a must see is the small uninhabited island of Poliaigos just opposite which has the best bays and waters in the whole of Greece. Anchoring and swimming there will be a special experience.

Day 6: Kimolos – Folegandros

Folegandros is still untouched thanks to its mild tourism development and is a perfect place to winddown and experience Cyclades food and architecture.

Day 7: Folegrandros – Santorini

Santorini the one of the most famous islands in the Mediterranean if not the most famous. Breathtaking when getting there with the yacht as the Volcano has created a natural bay with cliffs with the traditional Cyclades houses perch right on the top. If you have time, try to visit a winery as the wine that is produced here is unique due to the volcanic soil

Day 8: Santorini – Antiparos

Antiparos is an island that combines beauty with history and archaeological interest, and you should visit a small uninhabited island, Despotiko that lies just off the south east coast of Antiparos. Its rocky moonscape, with unspoilt beaches of all sizes, will offer you the chance to relax in absolute serenity.

Day 9: Antiparos – Paros

The island of Paros which is one of the most famous Greek islands with the exquisite beaches and small villages. The village of Naousa is perfectly protected from the winds and has a very vibrant atmosphere during the summer months while also having very good tavernas.

Day 10: Paros – Mykonos

Mykonos is the most famous Greek island and the most cosmopolitan. You must visit Little Venice, the Windmills and walk in the small streets of the town where the Cyclades architecture is at its best. Make sure that either after or before you arrive to go to the small island of Delos just opposite Mykonos. The island of Delos is one of the most important mythological, historical, and archaeological sites in Greece.

Day 11: Mykonos – Syros

Sail the town of Ermoupolis which is also the capital of the Cyclades. This was an old Italian colony so you will also see different architecture in the old town than other Cyclades islands. The two hills in the centre of the town one with the Catholic church and community and the other with Orthodox church and community make this island quite unique.

Day 12: Siros – Kithnos Loutra

Second stop at the the island of Kithnos but this time at the small port of Loutra where you can see the natural springs and baths while also relax in the small and picturesque marina. If you have time get a taxi and visit the main village of Kithnos which is inland and is very beautiful with its traditional Cyclades architecture and small streets.

Day 13: Kithnos – Kea

Kea is the first island of the Cyclades and last on your trip and a good stop as the port is protected from the North winds. You can either moore on anchor in the bay or on the small dock. You can rent a car or take a taxi to explore the island or just relax in the bay, definitely try the tavernas by the dock.

Day 14: Kea – Athens

Last day, enjoy your sailing back to Athens!

Delos

Delos is a UNESCO world heritage site, the centre of Greek antiquity. In the ancient times, the myth of god Apollo, god of light, and goddess Artemis having been born there rendered the island sacred: no mortal would ever be allowed to be born on its land. But, a cradle of gods as the island has been, no mortals would ever be allowed to die on it either. So, apart from it being a conspicuous religious and economic centre, the island had also been exclusive in that: even during the years of peak of the Delian Alliance, women on the brink of childbirth and people close to dying would be carried to the neighbouring island of Rineia. The whole of the known world of that age was aware of the sacredness of the island and of its uniqueness. Nowadays, Delos reserves its uniqueness to the know world: nowhere else in the Globe is there a natural insular archaeological site of this size and importance. No other island on Earth hosts so many monumental antiquities from the Archaic, the Classical, and the Hellenistic periods, i.e. the centuries of the great Greek art, on a territory used exclusively as an archaeological site. Delos is not a museum; Delos is not there to tell a story. Delos is history itself.

*Sailing tips* combine your visit to Delos with a short stay or even spend the night on anchor in the neighbouring island of Rineia.  

Santorini

Crescent-shaped Santorini (or Thíra), the precious gem of the Aegean, is actually a group of islands consisting of Thíra, Thirassiá, Asproníssi, Palea and Nea Kaméni in the southernmost part of Cyclades.

Did you know that the whole complex of Santorini islands is still an active volcano and one of the few in the world whose crater is in the sea? The islands that form Santorini came into existence as a result of intensive volcanic activity; twelve huge eruptions occurred, one every 20,000 years approximately, and each violent eruption caused the collapse of the volcano’s central part creating a large crater (caldera). The volcano, however, managed to recreate itself over and over again.

The last big eruption occurred 3,600 years ago (during the Minoan Age), when igneous material (mainly ash, pumice and lava stones) covered the three islands (Thíra, Thirassiá and Asproníssi). The eruption destroyed the thriving local prehistoric civilization, evidence of which was found during the excavations of a settlement at Akrotíri. The solid material and gases emerging from the volcano’s interior created a huge “vacuum” underneath, causing the collapse of the central part and the creation of an enormous “pot” –today’s Caldera– with a size of 8×4 km and a depth of up to 400m below sea level.

*Sailing tips* the island gets very busy during the summer months and berthing is quite difficult. Either just sail around the island caldera and enjoy the stunning views or the skipper leaves the crew to visit the island and remains on the yacht at anchor. 

Paros

Unrivalled natural beauty, beaches with crystal clear waters, unrivalled Byzantine footpaths connecting traditional villages and breathtaking landscapes make Paros, located at the heart of the Cyclades, one of the best loved holiday destinations in Greece. Parikia, the capital of Paros, is a beautiful Cycladic village with whitewashed cubic houses and impressive neoclassical mansions.   The Archaeological Museum displays exhibits from the island’s monuments (such as the Sanctuary of Asklipios and Pythios Apollonas, Delion etc.), including part of the “Parian Chronicle”, a chronological table of the 3rd century BC with references to important events and personalities of antiquity.

*Sailing tips* sail to the bay of Naoussa which is protected or the Piso Livadi port in the south side.  

Naxos

Naxos is the biggest and the greenest island in the Cyclades. It has high mountains, fertile valleys, lush green gorges, stunning seascapes and traditional villages perched high on mountain tops, where the inhabitants still wear their traditional dress and live off the fruits of the land. Naxos is also home to beautiful old churches, monasteries and Venetian castles coexisting harmoniously with the Cycladic architecture.

Upon entering the port of the whitewashed Chora of Naxos you’ll encounter the islet of Palatia at its entrance. On Palatia islet the impressive marble gate,  temple of Apollo, “Portara” stands still since the 6th century BC. According to mythology, the god Dionysus met Ariadni there, who had been abandoned by Thesseus.

Chora, the capital of Naxos, whose landmark is an imposing Venetian castle, is an old castle town with stone paved alleys (known as kalderimia in Greek) where you can admire a unique blend of Cycladic and Medieval architecture: mansions with Venetian blazons still decorating their entrances, narrow arched alleys (known as stegadia in Greek), catholic churches and fortifications.

*Sailing tips* although the main port and marina are protected from the North prevailing winds, it is advised to enter and leave the port either in early morning or later evening to avoid the waves and wind. 

Syros

This is the island where Greek tradition and western influence come to a harmonious marriage. Ermoúpoli (meaning “the city of Hermes”) is the island’s capital town and has been the first important trade and industrial centre of the country in the 19th century. Evidence of this glorious past can be seen on public buildings (the City Hall, the Customs Office, “Apollo” theatre), on the neoclassical houses and at the beautiful squares. Due to its economic activity, Ermoúpoli has been called “Manchester of Greece” and the history of its years of blossom is exhibited in the Industrial Museum.

The Orthodox community has contributed some outstanding religious monuments to the architecture of Ermoúpoli such as the churches of Metamórphossi tou Sotíros (Transfiguration of Jesus Christ), St Nicolas the Rich (Áyios Nikólaos Ploússios), Dormition of the Mother of God (Koímissis tis Theotókou).

The medieval quarter of the Roman Catholic community and the fortress-like St George’s cathedral are on St George hill, also named Áno Sýros (meaning upper Sýros). Go up the stairs to the top of the hill and through the narrow streets, by the traditional whitewashed houses, the archways and the open spaces with a breathtaking view of the island.

*Sailing tips* the main port is very picturesque but is busy with all ferries coming in and out. If you prefer a more calm surrounding sail to the port of Foinikas on the west side of the island.

Milos

One the most beautiful island of the Cyclades which was formed by volcanic activity in ancient years. You will find an exciting variety of gorgeous landscapes, beautiful white sandy beaches and volcanic rock formations. On the island you will find one of the most ancient mines in the Mediterranean.

As far as archaeology is concerned, Mílos is an ideal destination: the early Christian catacombs, a prehistoric settlement in Fylakopi and the mining museum (exhibiting 11,000 years of mining history) are definitely worth a visit.

You must visit as many beaches as you can! The white rocky landscape that embraces Sarakíniko forms an once-in-a-lifetime encountered lunar landscape while on Kléftiko, which can be reached only by boat, you can dive in secluded rocky caves with crystal clear waters. Add the wild beauty of Alogomántra, the open cave of Papáfragkas, the sheltered Ahivadolímni- the biggest beach on the island where also the island’s camping site is situated- and the beaches of Fyripláka, Yérakas and Tsigrádos adorned with grayish-red rocks.

*Sailing tips* sail to the neighbouring island of Poliaigos which has one the best bays for swimming off a yacht in Greece.

Serifos

Serifos Island, with its rugged mining sites, ladened with history, has its own distinct Cycladic flair. The island exudes a calm atmosphere and speaks directly to your senses. Despite its arid and wild land characteristics, Serifos is gracefully embraced by the deep blue colours of the Aegean Sea and has some magnificent beaches. The Imposing Chora

town is built amphitheatrically on a rocky hill commanding the island from the top. It is one of the most elegant Cycladic towns that will inspire you, even before your arrival to the island.

*Sailing tips* when at anchor or moored in the bay of the main port due to the morphology of the island you will feel the strength of the wind much higher than what it is actually at open sea. 

Kithnos

Also called “Thermiá” on account of its thermal springs, Kýthnos is very close to Attica; still, it is one of the less visited islands of the Cyclades. The island’s harbour (Merihas) and capital (Hóra) as well as Loutrá and Dryopída are located in the North. In the south, only the areas by the bay of Ayios Dimitrios and Panayia Canála are inhabited (where a famous monastery is situated within a pine forest).

The most impressive of the 65 sandy beaches of the island is Kolóna, where a lane of sand connects the islet of Ayios Loukas to Kýthnos. Low stone fences run for many kilometres on bare Cycladic hills with 350 white country chapels here and there.

*Sailing tips* when visiting Kolona Bay and wish to stay on anchor for a long time or even spend the night, prefer the east bay as the anchor holds better on that side. 

Kea

Due to its proximity to Attica, Kéa (also called “Tzia”) is an easily accessible beauty with a scenery variety: steep mountains, small fields, olive groves, vineyards, valleys, picturesque coves, exciting hiking trails and off-the-beaten-track beaches. On the island with the largest oak forest in the Cyclades bird-watching is a real delight.

*Sailing tips* sail to Vourkari and call one of the tavernas that are on the key (Aristos is a good choice) to keep a berth for you (if one is available). 

Sounion Bay

The temple of Poseidon, the ancient Greek god of the sea, dominates the southernmost tip of Attica, where the horizon meets the Aegean Sea. Perched on the craggy rocks of Cape Sounio, the temple is enveloped in myth and historic facts dated from antiquity until the present times.

There are stories about the ship of King Menelaus who stopped briefly at Sounio on his way back from Troy; or about the unfortunate King Aegeus who drowned himself on that spot and the Aegean Sea got named after him; or about the people who built a temple using local marble to honour the god of the sea and safeguard the profits from the neighbouring Lavrio mines.

*Sailing tips* the bay provides protected anchorage only to the prevailing North winds.