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Yacht sailing holidays & skippered tours in Greece

Discover more than 7 sailing holidays in Greece. Book a spot onboard and live 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 - Yacht sailing holidays & skippered tours in Greece

1900 reviews

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/15/2025

Elena L.

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Germany

Everything was simply perfect! The crew was incredibly flexible and accommodated all of our individual requests. We felt comfortable, well looked after, and completely safe at all times. The food was excellent and always freshly prepared for us. An all-around wonderful experience that we would repeat anytime. Highly recommended!
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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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Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/7/2025

Sharron G.

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United Kingdom

We were the last group to sail this year & enjoyed reading the other reviews as everyone had such positive feedback. We weren’t disappointed and although the weather wasn’t kind to us we couldn’t have had a better experience. Alessandro is an amazing skipper, he’s young but he’s been sailing forever & certainly knows his way around his boat and the waters & islands we sailed around. He made you feel safe & well looked after. Carlo couldn’t do enough for us all & his food & hospitality were excellent, making us laugh as we tried to speak Italian. We couldn’t believe how he was able to serve up the dishes from the tiny galley kitchen. Something different every day and he even caught a tuna & that was served up for lunch, you don’t get fresher than that. We couldn’t have had a better adventure with better crew. Thank you Alessandro & Carlo! PO5 will return xxxxx
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/6/2025

Corinne W.

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Switzerland

It was very nice and beautyful, when the sun was shining.☀️We had a good time and the crew was very nice, helpful. And kind. Thank you!

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