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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.

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 - Family sailing cruises yacht sailing holidays & tours in Cyclades

3 reviews

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

09/10/2024

maria m.

Spectacular trip with Alesandro great captain who took us to incredible places,,. every day in a new bay. Alexandro great person who took care of us at all times 🤩 we will 💪 repeat

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