South Western Cyclades Sailing Route

Sailing boat cruise on Paros, Sifnos, Milos, Kimolos, Poliaigos, Antiparos

Rent a yacht in Cyclades with a skipper


Islands hopping: Paros – Sifnos – Kimolos – Milos – Milos coastline – Poliegos – Antiparos – Paros

Suggested for: Couples and friends sailing, honeymoon, naturists sailing, gay sailing

Max sailing time per day: 6 hours

Min sailing time per day: 1 hour

Average sailing time per day: 3.6 hours

Miles in total: 120 – 130

  • 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

Interactive Map for Your Sailing Vacations in South Western Cyclades

Suggested West Cyclades route day by day

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 direct 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 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 to visit the catacombs and the village just under the catacombs , Plaka. Here you will see hundreds of caves used as private parking for the small boats.

Day #5

Milos Poliaigos. 15nm 3 (hours) today we are going to stay on 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 restaurants and continue with a drink at one of the locals bars. Night life here, especially at 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.


Contact and booking

Make your introductory reservation request to Greek Water Yachts for your skippered Greek sailboat rental, sending as an email at Greek Water Yachts team will respond within 24-48 hours.


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

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Apostolos V

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Greek Water Yachts
Paroikia Paros

Phone: +306932299490