Sailing the Cyclades

Cyclades Sailing Adventure


Taking as our base the island of Syros, the beautiful capital of the Cyclades, Tahita and her crew look forward to accompanying you on an unforgettable sailing journey…

Isolated beaches, an ancient civilization, uninhabited islands, unrivalled nightlife… there is an island for everyone… Let us tailor the ideal sailing trip for you!

Here is an example of what you will experience while sailing with us around the Cyclades islands:


DAY 1: Meeting at Syros, the capital of the Cyclades

Meeting at our base, the main port of Syros. Briefing and arrangement of provisions. Then we depart for Rinia, once a thriving ancient port, now a deserted island opposite the island of Mykonos – and according to myth the birth place of Apollo. We stop for a swim in the crystal-clear waters of one of the coves of Rinia. Spend the night on the anchor.


DAY 2: Sail to the archeological site of Delos and then to Paros

In the morning you can visit the famous ancient port of Delos. Then we sail to Paros island where we stop for an invigorating mud bath and a refreshing swim. We spend the night at the little fishing port of Piso Livadi where you can taste the local fish delicacies of Ηalaris.


DAY 3: Set sails towards the Small Cyclades & Iraklia island

Our first stop in the Small Cyclades is the wild and largely inaccessible island of Iraklia. Here you’ll experience the original life of the islanders and be able to follow an ancient path towards the south side of the island to explore the largest cave in the Cyclades. Supper at the main village where you can try Anna's famous goat stew and pies.


DAY 4 & 5: Sail to the pirate island of Amorgos

Next, we’ll sail to the tiny deserted island of Keros, known since ancient times when it was inhabited. Here we will stop for a swim, a chance to snorkel and a barbecue. In the evening we’ll sail to the pirate island of Amorgos, the famous setting for legendary film director Luc Besson’s "Big Blue".

The following morning you can try the steep climb up to the monastery of Hozoviotissa. This fantastic ancient building occupies a spectacular site on a cliff, suspended between the sky and the sea below. Then why not plunge into the turquoise, crystal-clear waters of Ag. Anna, below the monastery, and explore the Chora, one of the most picturesque villages in the Aegean. In the evening we'll visit the quaint village of Tholaria. When you’re there, your reward will be Mrs Maria’s home-made cooking while you listen to the local elders playing the violin and the lauto.


DAY 6: Spend the night on the anchor at Manganari beach, Ios island

Now it’s time to sail to Manganari beach in the remote south side of Ios island. You’ll have the opportunity to night dive through the phosphorescent plankton of the bay. Relax and enjoy the local fresh fish.


DAY 7: Last sail to volcanic caldera of Santorini

And lastly, we’ll sail and finish the trip under the cliffs of Oia in Santorini – famous for being one of the most amazing spots in the world to watch the sunset! Donkeys will be used to climb up the hill in case you don’t feel up to the never-ending steps to the village!

We’re as flexible as the weather!

The above itinerary is just an example of what you will experience while sailing with us around the Cyclades islands. Send us details of the islands you wish to visit, where you wish to start and finish you trip and let’s work together to create the ideal sailing journey for you.

Our skipper is highly experienced and happy to adjust the sailing trip according to what you are looking for in your holiday, of course, if the weather and other external factors beyond his control permit it. And never forget that those ”unexpected” surprises can often be the highlight of your trip!

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