Sail Cyclades

Cyclades Sailing

Sailing in the greek islands is the ideal vacation package for adventurous sea lovers. What makes cyclades sailing cruises in Greece the ideal vacation package? Mild and gradual changes in temperature, steady, predictable winds, an absence of tides and strong currents, crystal-clear waters and countless bays, a plethora of stunning islands and the short distances between them. What do you think? Is this the adventure you always wanted?

Day 1                                                        EMBARKATION at 12:00 pm                         Mykonos – Syros – Serifos

MYKONOS – SYROS (Duration: 3:00 hours)

Syros (pop. 21507) is located 78 nautical miles (144 km) southeast of Athens.

The largest towns are Ermoupoli, Ano Syros, and Vari. Ermoupoli is the capital of the island and of the Cyclades. It has always been a significant port town, and during the 19th century, it was even more significant than Piraeus. Other villages are Galissas, Foinikas, Pagos, Manna, Kini and Poseidonia.

The island was also the home of the philosopher Pherecydes, the teacher of Pythagoras. It possessed two leading cities, Syros (now the modern Ermoupoli) and another city on the western coast where stands to-day Galissas.

SYROS – SERIFOS (Duration: 3:30 hours)

Serifos is located in the western Cyclades, south of Kythnos and northwest of Sifnos. It is part of the Milos regional unit. The area is 75.207 square kilometers (29.038 qs mi) and the population was 1,420 at the 2011 census.

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 the ship docks, on your arrival to Serifos. You’ll get to visit two neighborhoods; Pano (meaning upper) Chora and Kato (meaning lower) Chora connected by a stairway. You’ll find some bars, cafés, and tavernas in the town’s narrow streets blending in with the whole scene harmoniously. It is worth taking a 10 minutes’ walk up to the Venetian castle, built in the 15th century, to drink in the view of the blue sea!

Day   2                                                                                                                                       Serifos – Kimolos – Milos   

SERIFOS – KIMOLOS (Duration: 3:00 hours)


This tiny and extremely beautiful island lies in the western part of the Cyclades, close to Milos island. Possessing a volcanic soil and a unique variety of minerals, it is famous for its fantastic beaches, ranging from thin sand to pebbles.
Kimolos is an island with rich history records. According to one tradition, it is named after Kimolos, the very first resident of the island.
More likely though Kimolos takes its name from the Greek word Kimolia, which means chalk. Both names recall the white rocks of the Island. And in effect, a white/silver quality of perlite is still being extracted today, along with cimolite, chalk.


The Mediterranean seal Monarchs monarchs’ haven is in the north and uninhabited side of the island. This is where you will find “Skiadi”, a natural sculpture resembling a gigantic mushroom. For those who are into thermal springs, go to the beaches of Ayioklima, Prassá (where they used to excavate chalk), Thérma and Kástro, the beach with the red stones.

KIMOLOS – MILOS (Duration: 0:30 hours)

Milos (pop. 4977) is a volcanic island in the south of Aegean Sea. The volcanic activity in ancient years has endowed Milos island with an exciting variety of gorgeous landscapes, consequently offering the visitor a wide range of activities. The funny shapes of the rocks and their wonderful colors at the beautiful white sandy beaches are one expression of the volcanic features of Mílos. the economic activity is another: minerals such as obsidian are excavated here. What is more, one of the most ancient mines in the Mediterranean is
on this island.

References had been made by Hippocrates to the peculiar morphology of spectacular caves (Papáfragkas and Sykiá) and a multitude of thermal springs (Kanáva, Alykí, Provatá, Pikropiyí).The diving enthusiasts will find a paradise in the underwater caves in the triangle formed by Mílos, Kimolos and Polýegos islands.

The island’s villages are lovely too: the stately Pláka (the island’s capital), the harbor of Adámantas, the beautiful Hivadolímni, the marvelous Emporiós with the little lagoon of Revary and the old iron mines.

It is famous for the statue of Aphrodite (the ‘Venus de Milo’, now in the Louvre), the statues of Greek god Asclepios (now in the British Museum), the Poseidon and an archaic
Apollo in Athens.

Day 3                                                                                                                               Milos – Polyaigo – Folegandros

MILOS – POLYAIGO (Duration: 2:00 hours)

Polýaigos is an uninhabited Greek island in the Cyclades near Milos and Kimolos. Its name
means “many goats” since it is inhabited only by goats. Its goat population maintains Polyaigos as a barren island. It has, however, some magnificent beaches, mainly on the southern part of the island, as well as many sea surface caves, which serve as a refuge to a dwindling population of Mediterranean monk seals (Monachus monarchs). A perfect location for snorkeling in deep blue waters.

POLYAIGO – FOLEGANDROS (Duration: 2:00 hours)


The port of Folegandros is the small village of Karavostasis. The Ano Meria village contains a small but interesting Ecological and Folklore Museum.
Shining under the Aegean sun, Folégandros was named after the son of king Minos. This off-the-beaten-path destination captivates the visitors with the untouched beauty of its beaches, the luminous blue of its waters, and the unadulterated style of its architecture.

The Church of the Assumption of the Virgin Mary
Towering above Hóra and with a stone path leading to it, a whitewashed impressive church awaits to be discovered. Allegedly built on the site of an ancient temple, the church hosts significant ancient immured inscriptions and statues’ pedestals in its yard and interior. Tradition has it that the silver-plated icon of the Virgin Mary is miraculous. Linked to pirate stories, the icon is carried around the town in a procession held every year on Easter Sunday.
Hiking tip: Follow the rocky path starting from Poúnda square all the way to the church (walking time app. 15 min).

Ano Merá

The picturesque village of Ano Merá is a traditional rural settlement of the 19th century. To learn more about the traditional everyday life of Folégandros, visit the Folk Art Museum (open from 17:00 to 20:00 in the summer).

Chrysospiliá is a natural monument of great interest, and not just to archaeologists and speleologists. Situated below the monastery of the Virgin Mary on a rocky beach at 30m above sea level with impressive stalactites and stalagmites, the cave is globally unique
for the ancient male Greek names written on its walls and roof dated back to the 4th century BC. Nicagoras, Themistocles, Cleon, Callimachus, Pythagoras, and Lysicrates are some of the names carved on the cave walls. According to some theories, the cave was used as a worship site where ceremonies for young men coming of age used to take place.

Day 4                                                                                                                          Folegandros – Sikinos – Santorini

FOLEGANDROS – SIKINOS (Duration: 1:00 hours)


It was known as Oinoe (Island of Wine) in Ancient Greece. It contrasts with nearby islands, such as Ios, in being quiet and relatively less developed. There are two villages, “Allopronia” on the south seaside, being the port, and another higher up in the hills being the chora.

The chora up on the hills is composed of two settlements adjacent to each other, “Castro” to the west and “Chorio” to the east. There are a handful of tavernas in the harbor. The beach at the harbor is one of two large sandy beaches on the island. Several ancient ruins rest on the island, although some are remote. There are two paved roads, although a third is being built to connect the nascent heliport and eventually a new resort on the other sandy beach, and there are several well-maintained dirt roads. Much of the island is very difficult to access due to the terrain. Nearly all of the island’s area is covered by terraces once used for extensive agriculture. Now only a handful are used across the island, most operating on government subsidies. The community had 273 inhabitants at 2011 census. It includes the uninhabited island of Kardiotissa and other uninhabited islets. Its total land area is 42.507 square kilometers (16.412 sq mi).

SIKINOS – SANTORINI (Duration: 2:00 hours)


Santorini, classically Thera, and officially Thira, is an island in the southern Aegean Sea, about 200 km (120 mi) southeast of Greece’s mainland. It is the largest island of a small, circular archipelago which bears the same name and is the remnant of a volcanic caldera. It forms the southernmost member of the Cyclades group of islands, with an area of approximately 73 km2 (28 sq mi) and 2011 census population of 15,550.Santorini is essentially what remains after an enormous volcanic eruption that destroyed the earliest settlements on a formerly single island, and created the current geological caldera.

Santorini is essentially what remains after an enormous volcanic eruption that destroyed the earliest settlements on a formerly single island, and created the current geological caldera.

The depth of the caldera, at 400m, makes it impossible for any but the largest ships to anchor anywhere in the protected bay, there is also a fisherman’s harbor at Vlychada, on the southwestern coast. The island’s principal port is Athinios. The capital, Fira, clings to the
top of the cliff looking down on the lagoon.

While visiting Santorini, we recommend a tour guide, who will take you on a ride through the history of the island, including a visit to the winery, which is an experience well to be remembered. Also, a walk through the town of Thira or Oia, for shopping, coffee or just sightseeing is always a favorite activity. If you wish we can arrange for you a beautiful café or an exquisite restaurant, including transfer, so you can admire the famous sunset of Santorini.

Day 5                                                                                                                                         Santorini – Ios – Amorgos

SANTORINI – IOS (Duration: 1:30 hours)

Ios is a hilly island with cliffs down to the sea on most sides, situated halfway between Naxos and Santorini.

Ios was the setting for the movie Ginger and Cinnamon (Dillo con parole mie). Also, scenes from the film Big Blue (Le Grand Bleu) were
shot in Manganari.The Port of Ios is at the head of the Ormos harbor in the northwest. From there the bus or a 15-minute walk up the steep donkey path takes you to the village, known as Chora. Chora is a white and very picturesque Cycladic village, full of stairs and narrow paths that make it inaccessible for cars of any kind.

The Port of Ios is at the head of the Ormos harbor in the northwest. From there the bus or a 15-minute walk up the steep donkey path takes you to the village, known as Chora. Chora is a white and very picturesque Cycladic village, full of stairs and narrow paths that make it inaccessible for cars of any kind.

Excavations on Skarkos hill unearthed a prehistoric settlement, proving that Ios has been inhabited since the early Cycladic period.
The island is said to have 365 churches and chapels, like the days of the year.

IOS – AMORGOS (Duration: 3:00 hours)


Amorgos is the easternmost island of the Greek Cyclades island group and the nearest island to the neighboring Dodecanese island group. It has a land area of 126.346 square kilometers (48.782 square miles), and a population of
1,973 (2011 census).The island features a lot of remnants of ancient

The island features a lot of remnants of ancient civilizations. At the time of Archaic Greece, there were three independent city-states there. They are believed to have featured autonomous constitutions but the same currency. Amorgos is distinguished by the size and quality of the walls surrounding the city of Arkesini, by the ancient towers whose remains are scattered all over the island, by the ancient tombs, the stone tools, the inscriptions, the vases and by other antiquities.

In recent years Amorgos became famous for the production of “Rakomelo”, which is a Greek mixed alcoholic drink, known in all of the Cyclades islands and especially Crete. It is a digestive spirit, high in powerful antioxidants such as flavonoids and is traditionally used by many Greeks as a home remedy for a sore throat or a cough. It is made by combining raki or Tsipouro with honey and several spices, such as cinnamon, cardamom, or other regional herbs.

Day 6                                                                                                                             Amorgos – Koufonisia – Paros

AMORGOS – KOUFONISIA (Duration: 1:30 hours)


Koufonisia consists of three main islands. Koufonisi or Pano (Upper) Koufonisi, Kato (Lower) Koufonisi and Keros. Geographically,
they are located on the southeast side of Naxos and on the west side of Amorgos and belong to the complex of the Lesser East Cyclades.
Uninhabited Keros is a protected archaeological site from which a large number of ancient Cycladic art pieces have been excavated in the 20th century.According to archaeological findings, Koufonisia

According to archaeological findings, Koufonisia has been inhabited since prehistoric times. Excavations in Epano Mili brought to light
evidence that dates back to the first years of Cycladic civilization. One of the most important findings from this period is a fryer-shaped vessel with a nine-ray star on it, exhibited in Naxos’ museum. Excavations on the east shore brought to light remain to date to Hellenistic and Roman times.Kato Koufonisi is located next to Pano Koufonisi,

Kato Koufonisi is located next to Pano Koufonisi, Shoinousa and Keros. It has an area of 4.3 square kilometers (1.7 sq mi) and it is almost uninhabited, as there are only a few rural houses exist. The most distinctive sight of the island is the small church of Panagia that is built on a jetty, on top of ancient ruins. Only fish and tourist boats anchor in its small, picturesque port anchor.

KOUFONISIA – PAROS (Duration: 3:00 hours)


One of the Cyclades island group, it lies to the west of Naxos, from which it is separated by a channel about 8 kilometers (5 miles) wide. It lies approximately 150 km (93 miles) southeast of Piraeus. Unrivaled natural beauty, beaches with crystal clear waters, unrivaled Byzantine footpaths connecting traditional villages and breathtaking landscapes make Páros one of the best loved holiday destinations in Greece. Its nearest neighbor is the municipality of Antiparos, which lies to its southwest.Parikía (Parikiá), the capital of Páros, is a beautiful Cycladic village with whitewashed cubic houses and impressive neoclassical mansions. A well preserved 13th century Venetian castle stands proudly on a hill at the center of the village offering an amazing view of Parikía. In the capital, you can also admire an important ecclesiastical monument, the 6th century church of Panayia Ekatontapyliani, also called Katapoliani. The name “Ekatontapylianí” means the church with 100 gates (“Ekató Pýles” in Greek), one of which is a secret one!

Parikía (Parikiá), the capital of Páros, is a beautiful Cycladic village with whitewashed cubic houses and impressive neoclassical mansions. A well-preserved 13th-century Venetian castle stands proudly on a hill at the center of the village offering an amazing view of Parikía. In the capital, you can also admire an important ecclesiastical monument, the 6th-century church of Panayia Ekatontapyliani, also called Katapoliani. The name “Ekatontapylianí” means the church with 100 gates (“Ekató Pýles” in Greek), one of which is a secret one!

Naoussa, a colourful village, where the ruins of a Venetian fortress stand at the entrance to its small harbour, lies at the north of Paros and is known for its exquisite shopping opportunities within the town’s narrow alleys, so a walk in town is recommended along the little fishing harbours and beautiful structure of the town. One can also take the opportunity to dine ashore at one of Cyclades finest restaurants.

Day 7                                                                                                                                Paros – Delos – Rinia – Ornos

PAROS – DELOS (Duration: 2:00 hour)

The island of Delos, near Mykonos, near the center of the Cyclades archipelago is one of the most important mythological, historical and archaeological sites in Greece. The excavations in the island are among the most extensive in the Mediterranean; ongoing work takes place under the direction of the French School at Athens and many of the artifacts found are on display at the Archaeological Museum of Delos and the National Archaeological Museum of Athens.

Delos had a position as a holy sanctuary for a millennium. Investigation of ancient stone huts found on the island indicates that it has been inhabited since the 3rd millennium BCE. By the time of the Odyssey, the island was already famous as the birthplace of the twin gods Apollo and Artemis. Indeed, between 900 BCE and 100 CE, sacred Delos was a major cult center, where Dionysus is also in evidence as well as the Titaness Leto, mother of the above-mentioned twin deities.

Delos is the archaeological site to visit if you are sailing in the Cyclades. There are guides to take you on a tour on the site, but it is generally better to organize it in advance. Swimming and diving are prohibited by law in Delos.

DELOS – RINIA (Duration: 0:15 hours)


Rinia or Rhenea or Rhinia, or Rineia was also known as Greater Delos, is an almost deserted island five miles SW of Mykonos. The anchorages around the island make a pleasant stop for people who avoid the noise of “civilization” and are a good overnight base prior to a visit by yacht to the archaeological site of Delos, from which it is separated by a 100-meter wide channel.

RINIA – ORNOS (MYKONOS) (Duration 1:00 hours)

Mykonos’ nickname is The island of the winds. Tourism is a major industry and Mykonos (pop. 10134) is well known for its vibrant nightlife and for being a gay-friendly destination with many establishments catering for the LGBT community. Archaeological findings suggest the presence.

Archaeological findings suggest the presence of the Neolithic tribe, Kares on the island in 3000 BC, but the first real settlers seem to be the Ionians from Athens in the early 11th century BC. Mykonos has many bays, like OrNos, which are well protected from the usual northern winds, in which water sports activities and snorkeling are possible. A walk through the main town is strongly recommended, with the typical Cycladic houses, alleys and windmills, the famous brand stores, the never-ending nightlife and the exclusive restaurants, being the trademark of Mykonos.

Day 8                                                         DISEMBARKATION at 12:00                                               Mykonos

THE END