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Yacht sailing holidays & skippered tours in Greece

Discover more than 3 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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

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

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

2164 reviews

Sailing paradise in Greece on a big 50 ft boat: the best local experience

10/6/2026

Iris D.

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BE

Such a wonderful experience! As a solo traveller I had a great time during this trip, Aga and Arnon were very welcoming and took good care of us. The places we visited were stunning, the food Aga prepared for us was excellent, and the overall vibes were 10/10.
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

10/6/2026

Marcos B.

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US

Alessio was a great host/skipper and I had an amazing week with him and my other "boatmate" passenger, Victoria. The boat is stunning and I booked a cabin to myself which had its own private bathroom. If you're traveling alone, that's the way to go. Weather didn't cooperate much but I was there for the experience on the boat which was exactly what I got. Alessio is very skilled in handling the boat.... and a great cook! All in all, can't recommend Alessio and his boat, [hidden] enough. Grazie mile, Alessio :)

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/6/2026

Thomas S.

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DE

Andrea & Caroline let us experience a very nice holiday week. Andrea as skipper, who not only has excellent local knowledge of the islands, beaches and local conditions, but also always made sure that it was safe and comfortable on board for us as inexperienced sailors. Caroline's role as a fairy godmother on the boat ensured that the physical well-being was never neglected, culinarily the dishes, breakfast and lunch were simply first-class beyond any expectation. She not only made sure that you felt very comfortable, but also showed very quickly with many little things that she pays a lot of attention to her guests, their preferences and wishes. This was a very pleasant, relaxed week, which I can only recommend, so also my fellow travelers have expressed. After a very short time, you have the feeling that you are not just a guest, but rather a good friend who is visiting. I can only highly recommend it, with Andrea & Caroline we were in competent, courteous & hospitable hands. Thank you very much for that and best regards to Crete.

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

10/6/2026

Victoria S.

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GB

A fantastic week of sailing, good food and good company. Alessio was really helpful in all aspects of the trip. The boat was very cosy, well equipped and comfortable. Would recommend to anyone who wants to try a sailing holiday for the first time.

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