Call Us Today! +30 6932299490 & +30 6977206845|

Greece sail tour / Cyclades sailing trips

/SW Cyclades sailing tour
SW Cyclades sailing tour2018-10-06T13:36:12+00:00

South West Cyclades Sailing Tour

Wonderful beaches, exciting landscapes, a rich history, white-washed Cycladic villages and fine food are the highlights of the places you will visit during the tour

  • this is a route that you have to take if you love sailing and love a stunning coastal scenery

  • it is a combination of some bigger islands, like Milos, with some tiny, quite places, like Kimolos and Poliegos

  • some of the sailing legs are long, ideal for the experienced sailors but also some short legs to nearby islands.

  • distinctive topography and the pattern of some of the islands is due to the caldera of a volcano of the Pliocene period.


Islands hopping: Sailing the Cyclades islands, Paros –> Sifnos –> Kimolos –> Milos –> Milos coastline –> Poliegos –> Antiparos –> Paros

Duration: 7 days

Suggested for: Couples and friends sailing, honeymoonnaturists sailing

Dates you can do this trip: May, June, July, August, September, October

Max sailing time per day: 5-6 hours

Min sailing time per day: 1 hour

Average sailing time per day: 3.6 hours

Miles in total: 120 – 130

Sailboats you can pick:

  1. Beneteau40 sailboat(2 – 4 guests)
  2. Benteau50 sailboat(up to 8 guests)
  3. Lagoon39 Catamaran(up to 8 guests)

2019 Prices:

Prices in €/week for skippered charter October May, June & September July & August
For 2 people 2550 3100 3400
For 3 or 4 people 2950 3400 3700
Departure / Arrival Paros/Paros
What the package includes VAT 12%, the sailing yacht with all her equipment, skipper’s fee, taxes, insurance, credit card commission
What is not included food & drinks, the diesel(depends on the consumption), the marina’s fees at the islands that you are going to visit and the end cleaning.From our experience for one week charter this amount is about 260€ in total.
Prices in €/week for this skippered charter May June &
July &
Up to 6 persons 3600 4100 4700 3500
For 7 or 8 persons 3900 4450 4950 3800
Departure / Arrival Paros/Paros
What is included yacht, skipper, VAT, insurance, taxes, bedding, linen & towels, cooking fuel, motorised tender, watermaker, AC current for charging your small devices, CD & MP3 sound system, end cleaning.
What is not included 1. food & drinks
2.the diesel(depends on the consumption), the marina’s fees at the islands that you are going to visit and the end cleaning.From our experience for one week charter this amount is about 240EUR in total.
Prices in €/week for skippered catamaran charter May & Oct June & Sep July Aug
Up to 6 guests 4600 5600 6100 6400
For 7 & 8 guests add 5% for each person
Check in / Check out Paros at 17:00 / Paros at 09:00
What is included catamaran Lagoon 39, skipper, insurance, VAT, taxes, bedding, linen & towels, motorised tender, AC current for charging your small devices, end cleaning.
What is not included 1. your food as well as your skipper's is at your charge.
2.fuel-water-port taxes (in total approximately 400 € per week depending on the fuel consumption) card commision





Sailing the Cyclades


Greek Water Yachts

Interactive Map for Your Sailing Vacations in South Western Cyclades


Route info

The check-in at 11:00 and check out at 17:00 is for the Beneteau40 and Beneteau50. The Lagoon39 check-in is at 17:00 and the check out at 09:00

Day 1: Meet your skipper at the Marina cafe at 11:00 and board the sailboat. After the briefing concerning your trip, set sail around Paros for our first destination, Sifnos. 

Paros – Sifnos (Platis Gialos) 22nm (4 hours). We sail directly in the marina. Platis Gialos has a wonderful long sandy beach nearby with nice taverns and charming coffee shops on the seafront. You can visit the local pottery shops and see live how they make the pots, dishes, and other articles made of earthenware or baked clay. Also, you can rent a car-bike or take the bus and visit the capital of the island, Apollonia. Try the local goat meat from the nearby island Kitriani cooked in clay pots.

Day 2: Sifnos – Kimolos: 12nm (2.5 hours). We are going to make two stops for swimming ( Fikiada – Sifnos) and Prassa( Kimolos). Kimolos means chalk and you will enjoy a special white view of all the chalk mines all around and also a special formation of the rocks, like “the elephant”. At the port, you can find charming taverns but we strongly recommend to walk up to the village 2km away which is really beautiful. Try local dishes and ask for “ladenia” something like pizza but cooked in their own way.

Day 3: Kimolos – Milos 15nm(3hours) we are going to stop for swimming in a lovely place called Ellinika with underwater antiquities. In this area, they have found the famous statue of Afrodite of Milos in the sea. At Adamas the main port of Milos you can find anything you are looking for, taverns restaurants bars supermarkets and so on. We recommend you to rent a car bike or take the bus and visit a wonderful spot called Sarakiniko. A unique place with white rocks that can have amazing shapes often compared to a moonscape. Finish your day at the capital of Milos Plaka enjoying a wonderful sunset drinking a mojito.

Day 4: The round of Milos up to Kleftiko 26nm (6 hours). Today we are going to explore the wonderful west coast of the island with the hundreds of beaches up to Kleftiko. Kleftiko is a place accessible only by boat with a unique beauty. The complex of these volcanic original rocks is a magical landscape worthy of admiration, and also a part to enjoy the sensation of the transparent blue-green waters and the sun. Kleftiko used to be an old hide-out for pirates from where the pirates’ ships used to pass and anchor so as to get protected in its small creeks and imposing rocks. In the afternoon we will return to Adamas again. Its recommended visiting the catacombs and the village just under the catacombs, Plaka.

Day 5: Milos Poliaigos. 15nm (3 hours) today we are going to stay on the anchor for the night. Polyaigos is an uninhabited island full of goats. Here you can experience all the variations of blue and green in the sea, peaceful night and white rocks in amazing formations. Be prepared with food on board because there is no tavern.

Day 6: Poliaigos – Antiparos 32nm (6hours). Stop for swimming at Despotiko and overnight at Antiparos town. Antiparos is the last island of our cruise. Wandering around the small streets of the beautiful village, have dinner in one of the hundreds of restaurants and continue with a drink at one of the local bars. Nightlife here, especially in high season is a must for everyone.

Day 7: We strongly recommend you before setting sail for our final destination, to visit the cave of Antiparos. Buses are operating just 100 meters away from the yacht. On your return on board, we will leave immediately for a nice anchorage at a small island north of Antiparos with crystal clear water. The afternoon has already come as well as the farewell time at Paros port.

Meet the islands

Sifnos in a few words: According to the legend “Sifnos” was the name of the son of the Attic hero Sounios, and the island was named after him. According to another version the appellation Sifnos derives from the adjective “sifnos” that means “empty” because of the many underground mine galleries in the subsoil of the island.Sifnos is not known only for its natural beauty but it is also famous in the whole world for its pottery.

Location: Sifnos is part of the island complex of the West Cyclades, in the Aegean Sea and it is situated at the centre of the triangle, which is set by the islands Serifos, Kimolos and Antiparos.

See :

  • The capital of Sifnos Apollonia spreads amphitheatrically along three hills in the center of Sifnos.
  • In Sifnos you shall see places, such as the noble Artemonas, the fascinating Vathi, the beautiful Faros, the magic Chrissopigi, the cosmopolitan Platis Gialos, the picturesque Cheronissos andKastro, where the picturesqueness and the simplicity of life are beyond any imagination. You shall be enthusiastic over the arrangement of the mansions and the simple houses, with the paved courtyards and the arches. The invariable beauty of the entire island!

Do :

  • Hiking , Sifnos is the ideal island for those who like walking. The fans of walking will have the chance to follow many alternative paths.
  • To enjoy the rare beauty of the landscape of Sifnos, you must walk in the old scenic paths as several areas have no alternative access. Only by path you can visit Agios Sostis with ancient gold mines, the ancient acropolis of Agios Nikitas in Seladi, Prophet Elias Apsilos (means the tall), Panagia Tosso Nero, most of the 76 scattered on the island ancient towers (6ou- 3rd cent. BC)
  • Sports / activities : At the beaches of Platis Gialos and Vathy, there are rental agencies for canoe and other water sports. There is also a educational centre for diving.
  • For the lovers of photography, Sifnos is the ideal place to offer themes to shoot! Its landscapes, the blue of the Aegean, its architecture, its monasteries and churches…
  • Visit the potter workshops.
  • Enjoy your drink in a relaxed atmosphere at the beach of Platis Gialos, Faros, Vathy, or Kamares or choose the unique atmosphere of the café-bars in Kastro and Artemonas.
  • Do not loose the opportunity to visit a local feast in order to meet the customs and tradition of the island.

Eat- drink : Sifnos is the homeland of the great chef Nikos Tselemendes, and its cuisine is delicious, with traditional dishes! As for its pastry making, all you have to do is take a walk in its traditional bakeries and workshops and discover for yourself its authentic tastes!

Read More:

For more information check Sifnos at wikitravel

Kimolos In a few words : Kimolos means chalk and you will enjoy a special white view of all the chalk mines all around and also special formation of the rocks , like “the elephant”.

Location: Kimolos is located on the southwestern edge of Cyclades.
See :

  • Visit the village Chorio. The the older residential of this village  part is the medieval castle, of the 14th or the 16th century. Also, visit there the Church of the birth of Christ. The houses in Chorio village are build with the hard rock of the area (sideropetra), while there are decorative details of limestone.
  • Visit the archeological museum  located at Chorio. Impressive and worthy of mention is the crystal, transparent floor on which you can walk and underneath it see a reconstruction of an ancient burial, as it was found in the excavations.Among the exhibits there are: a gravestone of a headless woman, carved on local rock, from the oldest in Greece (8th century BC), a headless female statue, 1.30 meters high (2nd century BC
  • Visit the Folk and Maritime Museum which is located in the castle of Kimolos. The aim of the Museum is to save and preserve whatever has been left of the old heritage and popular culture of Kimolos

Do :

  • Walk around the villages and admire the primitive, authentic beauty of the island.
  • Visit the beaches Rema , a natural swimming pool, “Sirmata” (caves, carved into the soft rock , Karas , suitable for diving, Prasa ,amazing beach with white, thick sand (both in and out) and turquoise waters also many others beaches are waiting for you at summer time.

Eat – drink :

  • Taste The most well known local dish is Ladenia, a unique product made of dough, fresh tomato, onion and olive oil.
  • You can buy excellent honey, xino (sour fresh skim-milk cheese), manoura (dry cheese wrapped with grapes must), small cucumbers (round, with stripes, crispy that are sweet when ripe), caper and tomato paste.
  • At the taverns you can find fresh pasta of Kimolos, tomato meatballs and Greek salad with cucumbers of Kimolos and xino.

Read More:

For more information check Kimolos at wikitravel and our article or charter a yacht from Greek Water Yachts and discover Kimolos on your own.

Milos in a few words: Milos was an important center even before the Minoan era, because of the volcanic ground and especially obsidian (a black, hard, volcanic rock that was used to manufacture weapons and tools). Because of the fact that the statue of Aphrodite was found on the island, there is the myth of worshiping the goddess and her relationship with Milos.


  • Visit Klima a traditional settlement near Plaka where you can see the “Syrmata” The «sirmata» (wires) are the characteristic two-storey houses of Milos, which are built on the seafront in order to store the fisher boats. Now most of the wires are being rented or are small shops with traditional products and souvenirs.
  • In 1820 in a field near Klima a farmer dug the statue of Venus de Milo, which is now displayed in the Louvre Museum in Paris.
  • Visit the Catacombs of Milos are the first major Community cemetery of the early Christian times. The Catacombs were used as a cemetery but also as a place of worship, as the piece of rock has been left in place in the middle of the gallery B to serve as an altar, proves
  • Visit The Venetian Castle of Milos. The castle was built in the 13th century, on the hilltop which now is the Plaka, the capital of the island. Around the castle you will find several churches including the Assumption of the Virgin Mary or Skiniotissa and the church of Panagia Thalassitra.
  • Visit the ancient theatre of Milos located in the area of Tripiti.
  • Visit the archeological museum of Milos in Plaka. you will see mainly exhibits of two periods of prosperity for the island. The first is the prehistoric period and the second starts from about 1.000 BC up until the early first century AD.
    Next to the main road towards Pollonia and just before you get there you will find one of the most important archaeological sites in Greece, the ancient settlement of Phylakopi. Visitors have the opportunity to see a great part of the cyclopean wall


  • Thermal Baths . Milos is located very close to the volcano of Santorini and because of the post-volcanic activities it features several hot springs.
  • Explore the breathtaking beaches : Kleftiko, Gerontas, Gonatas, Tsigrado, St. Kiriaki, Fyropotamos, Mandrakia , Sarakino and many others. Because of the volcanic , the strong winds and the waves there are many secret and buys and beaches sculptured as a part of this unique landscape. You will find a beach next to an archaeological site, to a traditional settlement, near next to a castle, next to minor or a totally ditached beach made for you.
  • Do water sports or diving in well organized beaches.
  • The island offer a large variety of restaurants, café, bar, tavernas for an intensive or relax time at day or night.
  • Shop in the countless little shops of the island where you can find an Aphrodite of Milos, Greek style clothes. Wines and whatever else you wish.

Eat – Drink: Taste fresh fish and seafood and suggest delicious and original dishes, such as soups and caramel flavored with thyme, squid donuts with sweet and sour sauce, carpaccio of fish of the day marinated in lime and red mullet fillet with citrus sauce.

Read More:

For more information check Milos at wikitravel 

Milos Greece from Greek Water Yachts on Vimeo.

Poliegos In a few words : Poliaigos means the place which is full of goats. It is an inhabited island, the only habitants are a shepherds couple. Polyegos is particularly important scientifically and ecologically and has joined the  Natura 2000 European project.

Location: Polyegos is a small isle ,half the size of Kimolos and at a short distance, (1 mile). Administratively It belongs to Kimolos. This is the best preserved geological island in the Aegean
See : Very interesting is a cave at the south west side of the island, the cave of Agios Georgios, but you have to walk for more than two hours from the port to visit it. The bay of Alimia at the south west coast has a lovely beach and also a sunken battle plane from the second world war , visible from the surface.

Do :

  • In the center of the isle , there is a small valley with an old settlement and an old, open cast mine of baryte.
  • There are plenty of beaches for visitors to swim . Once on the island, you can swim at Pano Mersini, at Kato Mersini , at Armoura or at Panagias Avlaki
  • There is a church of “Kimissis Theotokou” (Assumption), which was part of a monastery founded in 1622 , now lying in ruins.
  • Visit the lighthouse and Diamantospilia (a cave with fine crystal quartz and other nice minerals).
  • If you are lucky, you will meet some flocks of wild goats.
  • Sail around the island with a boat . It will be unforgetable!!!

Read More: For more information check Poliegos at wikipedia

Antiparos in a few words: A very small and beautiful island which has direct relation with the big sister, Paros.

Location: Very close to the west coast of Paros.


  • The Antiparos cave where you can go by bus from the port.
  • Despotiko island where there are a lot of archaeological see sights.


  • swim at the wonderful beaches all around the island, especially in Agios Georgios beach.
  • Visit the local festivals during summer.
  • Many bars, cafe and clubs for nights that never be forgotten

Eat – Drink: Taste traditional specialties in any type of restaurant you wish.

Read More: For more information check Antiparos at wikipediawikitravel 

Paros in a few words: For most travelers at Cyclades islands, Paros is the most beautiful island of the area. Once you visit the island you fall in love with it and promise to come back again. Paros can satisfy the most demanding traveler. Gorgeous golden beaches all around the coast, traditional settlements, sports activities, nightlife for all interests are some of its characteristics.

Location:The location of the island in center of Cyclades and near Naxos, Ios, Sifnos, Mykonos, Santorini and Syros is ideal for private sailing excursions  and trips around at the nearby islands and the connection with the mainland. That’s why Greek Water Yachts offer it’s crewed sailboat rental services in Greece from Paros.


  • Panagia Ekatontapiliani  in Parikia.
  • Naousa (Greek: Νάουσα) is a village in the north eastern corner of the island.
  •  Lefkes village is in the middle of the island with many nice tavernas, and beautiful alleys.


  • Visit as many beaches as you can, don’t stay in one every day.
  • take a very nice walk at the old stones of the Byzantine Route down to Prodromos.

Eat – Drink:

Select a place you like and taste:Gouna fish, Local cheese ,Kapari ,Souma ,Ntakos ,Octapus

Alternatively you can arrange with the crew of the sailing boat a Greek dish with local products

Read More:

For more information check Paros at wikipedia, wikitravel.

Booking form

Make your introductory reservation request to Greek Water Yachts for your skippered Greek sailboat rental by filling out the contact – booking form.  We will respond within 24-48 hours.



Check out our questions and answers section about common questions concerning your sailing trip to Greek islands, Cyclades with captain.



Private yacht charter Milos, Kimolos, Sifnos, Poliegos


Greek Water Yachts