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Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 10 opportunities to get on board a Sailboat 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 - Sailboat yacht sailing holidays & tours in Cyclades

380 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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Sailing in the Cyclades

09/9/2025

Jana H.

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Germany

Our very first sailing trip turned out to be an unforgettable great experience! Great boat, interesting excursions, delicious food, and most importantly with skipper Yann the dearest and most caring person you could wish for! We like to remember all the experiences (including the card games that were new to us) and all your unexpected surprises on a boat. A big thank you (unfortunately without blue flip-flops 😉) Jana and Flo
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Sailing in the Cyclades

09/9/2025

Giovanni P.

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Italy

Great!
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Fast cruising Cicladi Occidentali

09/8/2025

Beatrice D.

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Netherlands

Annalisa and Lorenzo welcomed me on their boat and made me feel at home from day one. They made me discover the beauty of the Cyclades with its crystal clear waters and magical sunsets. They filled the days with their stories and delicious food! It was an unforgettable holiday and I will definitely come back for another trip with them!

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