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Family sailing cruises yacht sailing holidays & tours in Cyclades

Discover more than 1 opportunities to get on board a Family sailing cruises adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

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The world's largest marketplace for sailing holidays

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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 - Family sailing cruises yacht sailing holidays & tours in Cyclades

5 reviews

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Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

09/15/2025

Florian H.

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Germany

Great trip & great skipper!
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SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades

08/2/2025

Filippo F.

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Italy

The islands visited and the sea were truly splendid. For this reason alone, the holiday was worth it. The boat was large, in good condition, but perhaps there were a few too many of us to fully enjoy the spaces: even on the foredeck it was difficult to find room for everyone, and with five women on board, that area was often off limits. The skipper proved to be competent and serious even though it was not George and it is fair to say that because we only found out once we got on the boat. Too bad for never having done the roadstead, the proposed tour was beautiful but it seemed a bit like a tour de force with a very tight schedule of arrivals and departures from the various ports, something that had never happened to me in other boat holidays because generally because of the philosophy of the trip we have always been a bit free to decide whether to do port or to anchor, when to leave and when to stop if we saw something interesting. In addition, the total absence of wind forced us to always move with the engine, which took away part of the charm of sailing. In general, though, the atmosphere was friendly, and everyone behaved with kindness. If I had to recommend George, I would say that he is a reliable person
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SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades

07/22/2025

Manuel R.

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Canada

Very nice first sailing experience for our family, the Skipper was perfect (Franco Greek), advised us on the best destinations in the small Cyclades. The sailboat was very good and functional. Thank you to Georges for the welcome and the organization. I recommend this experience to visit the islands in the best way.
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Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

09/15/2024

Rafael G.

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Spain

Alessandro is a great !!

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