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Private yacht sailing holidays with skipper in the Cyclades

Visiting the Cyclades islands by hiring a sailboat will be one of the most beautiful experiences you can do. Choose between sailing, catamaran and gulet and let yourself be conquered by the contrast of the blue and white of Mykonos, Santorini, Paros and the Little Cyclades.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Private yacht sailing holidays with skipper in the Cyclades

76 reviews

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Sailing in the Cyclades

10/12/2025

Lisa B.

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Germany

Yann has a great and modern boat and always surprised us with culinary delights - whether on board or ashore. The excursions and activities were very varied and we enjoyed the tavern visits very much. Linguistically, it was not always easy for us in the group, as almost all the others in the group, like Yann, were native speakers of French or knew the language and then often switched to French in group situations with each other, where we felt left out and often had the feeling that we didn't notice the plans. That was a bit of a shame. Yann is an experienced skipper, we always felt safe - he knows the Cyclades very well and we were able to explore great bays and places. However, we caught a week with quite strong winds, which brought us as beginners to some limits (seasick) - we personally would not have had the ambition to cover such long distances under these circumstances. All in all, we had an intense adventure, which we remember with many highlights. :) thank you
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Milos to Paros: the best of the Cyclades

09/27/2025

Rocco G.

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Switzerland

Alessandro is a legend, an excellent cook and tries to fulfill customer requests in the best way always taking into consideration the safety and comfort of the crew. You feel like you care about delivering the best experience possible. We had bad luck with the weather, but despite this it was an adventurous and nice week.
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From Paros to Milos, the hidden gems of Cyclades

09/24/2025

Anna B.

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Germany

The best sailing trip we could have wished for. Nikos knows the waters and his boat by heart. Even with weather changes he brought us to the sweetest spots of the Cyclades. Besides his technical skills he is a fun and welcoming skipper that considers the wishes of the crew at all times.
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Milos to Paros: the best of the Cyclades

09/23/2025

Massimiliano B.

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Italy

Alessandro, in addition to being a dispenser of seafaring anecdotes and an excellent "skipper" was above all a very nice travel companion.

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