Santorini whitewashed village

Cyclades Sailing with a skipper

Cyclades Sailing; a 14 days Mykonos-Santorini-Milos sailing itinerary.

The ultimate plan for the itinerary “Cyclades Sailing”, yet we do recommend that itineraries be kept flexible. Every itinerary is subject to various factors such as weather conditions or a change of heart. As always every pre-planned itinerary, with the exception of the Port of Departure and redelivery, may be altered in consultation with the Skipper. To thoroughly enjoy the richness of the Cycladic islands you need at least 20 to 25 sailing days. But with 14 days you get much more possibilities, including Mykonos, Santorini, and Milos.


Sailing down to Mykonos

DAY1 (Saturday): We will start our sailing tour in Athens where you will be welcomed on board on Saturday afternoon with a welcome cocktail. Provisions have been organized based on your wishes and after finishing the paperwork we will sail for the bay of Sounion were we will spend the night on anchor.

DAY2: After breakfast, there will be time to hike to the temple of Poseidon. Upon return we set sail to Kea were we will spend some time in a bay on anchor for a relaxing swim and lunch. After lunch, we move to the main port where we will arrive late afternoon.

DAY3: We set sail to Siros, as this is the center of the Cyclades it plays an important commercial role. In Ermoupoli where we will dock for the night, you can see the glamour of the past that reflex in the great architectural monuments. Of course, we will stop on route for a swim and lunch!

Cyclades Sailing: The temple of Poseidon, an important anchorage before setting sail into the Cyclades.

Cyclades Sailing: The clifftop Temple of Poseidon at Cape Sounion, the southernmost tip of the Attica peninsula


DAY4: Today we sail to Mykonos. We will go directly to the marina of Mykonos. You will have the whole day to explore the island. If it is too windy we will anchor on the south side of the island and. There are plenty of restaurants and nice coffee bars on Mykonos and a small exploration of the main town is worthwhile.

Sailing from Mykonos to Santorini

DAY5: Leaving Mykonos we head for Delos. The island of Delos used to be the place of worship in the Cyclades and is now one of the most important mythological, historical and archaeological sites in Greece, but it can only be reached by boat. After you explore Delos we will sail down to Paros and spend the night either on anchor or in the port of Naousa.

DAY6: From Paros, we sail down to Ios or Iraklia. The Chora on Ios is a white and a very picturesque Cycladic village, full of stairs and narrow paths, that makes it inaccessible for cars of any kind. Today, however, the main path through this village is completely taken over by tourism in terms of restaurants, boutiques, bars, and discothèques most of them servicing a ‘younger’ crowd. Iraklia is a small yet beautiful island between the islands of Naxos and Ios and part of the Small Cyclades. The port is small and it has an authentic Greek way of life.

Cyclades Sailing: Sheer cliffs on the north side of the main village Chora.

Cyclades Sailing: Beautiful panoramas from Folegandros Chora


DAY7: Leaving early we will head for Santorini. We spend lunch on a swinging mooring under the town of Oia (Pronounced like I-A). During the afternoon we will do some sightseeing in the crater of Santorini and you may have a bath in the hot springs close to the Caldera. In the afternoon we head for the South side of Santorini where we spend the night on anchor.

Sailing from Santorini to Milos

DAY 8: A free day to explore Santorini. As the island is not that small and pretty hilly you might want to rent a car so that you can explore the island from the Red Beach to the sunset in Oia. We anchor just off the coast from Akrotiri. Akrotiri is an ancient city that was covered in a heap of volcanic ash in the late 17th century B.C., preserving it for present-day archaeologists and interested tourists. The site is so well preserved that it is often referred to as the Pompeii of the Aegean.

DAY 9: We will leave early today so that we can explore Sikinos, for lunch and a swim, and Folegandros for the night. The Chora of Folegandros is closed to car and motorcycle traffic and has a unique “center” of three squares in a row, with trees under which to enjoy a drink or food in a quiet, romantic atmosphere. Bougainvillea and hibiscus color the small wooden balconies around the old Kastro (XIII century). The panoramas from the Chora and beautiful situated Church of Panagia Source are breathtaking.

DAY 10: From Folegandros, we sail west, to Milos. Depending on when we leave and the wind/weather we will find an anchorage for swimming and lunch on Kimolos or Polyaigos. We end up late in the afternoon in Adamas, the main port of Milos. We can choose to visit the Plaka and enjoy our dinner there or at one of the tavernas at the sea.

From Milos, we head up and return to Athens

DAY 11: We circumnavigate Milos today and end up in Sifnos for the night. Milos has a very rough coastline with lots of caves and hidden beaches. We visit Kleftikos, an impressive spot that can only be reached by sea. The legend says that one of the caves in Kleftiko was a pirate hideaway and that they had hidden in there their treasury, but it was never found.

DAY12: From Sifnos, it is only a short sail to Serifos. We can spend more time on an anchor for lunch or explore the port where we will spend the night. From the port of Livadhi, a large natural port, you can take a bus (or a quad/scooter) to the Chora. The chora build on the hillside and is overlooking the port and a part of the island. You can also hike to and of the nearby beaches.

Cyclades Sailing: Milos has many interesting places to visit by boat, like the caves of Kleftiko.

The Kleftiko caves are the perfect hideout for the pirates “kleftis the Greek word for a thief”


DAY 13: Kithnos is the last island of the Cyclades that we will visit, and we will spend most of our day in the bay of Kolona. This is a beautiful double bay with a small sandy beach in the middle. The night we can spend on anchor or move to the port of Merichas. In both cases we can have our last island supper in a taverna, it is the perfect last day on the islands.

DAY 14: We return to Athens and will be back in Athens at around 18:00 o’clock. You can spend the night on board or we can book you a Hotel in the city of Athens. If you never stayed in Athens we suggest staying at least two more nights in Athens (not included).

DAY 15: (Saturday): Check-out at 9:00 o’clock.

Cyclades Sailing. The deep blue sea, have you ever jumped in water that are a couple of hundred meter deep!

Enjoying a dip in the middle of the Aegean… only a couple of hundred meters deep 😉


Last words

The itinerary is totally flexible and sailing clock-wise (like described) or anti-clock-wise is possible. We can sail this trip in any sailing yacht or catamaran of your choice. The size is depending on your party size and budget. You will sail with a skipper/tour leader and a hostess/ cook is optional. If you sail with a hostess/cook you won’t have to worry about cleaning and organizing the boat. The cook will also take care of the shopping based on your wishes, of course!

Contact us for more details, prices and any other questions you might have for our “Cyclades Sailing” trip! I will be happy to answer any questions you might have.

Cyclades sailing, Cyclades Sailing with a skipperWalter Kruk