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Yacht sailing holidays & skippered tours in Greece

Discover more than 1 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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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

1849 reviews

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One-way flotilla in Ionian Greece from Zakynthos to Lefkas

08/29/2025

Federico D.

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Italy

We had a beautiful sailing trip in Greece! ⛵️ The skipper Matteo was really good, super prepared and always very kind to everyone. The group was very nice and united, we had a lot of fun and the places we visited were really beautiful. 🌊✨ The only negative note: the boat had some technical problems, in particular the bathroom that did not work well. For the rest, however, the experience was excellent!
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Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

08/27/2025

Niccolò C.

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Italy

Arthur is an experienced navigator who knows how to take you to beautiful places suitable for the wind of that moment.
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Sailing from Corfu to Zakynthos in 7 days

08/27/2025

Kendra B.

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Italy

I have been sailing on sailboats for several years now and I can say without a shadow of a doubt that Max was one of the best skippers I have had the opportunity to meet. He proved to be a cheerful, funny, very professional and cautious person in navigation and mooring. I greatly appreciated his ability to manage all events, including the unexpected, with a tranquility and calmness that is not at all obvious. You can feel that this also derives a lot from his great experience, and this allowed him to convey great calm and a sense of security to the whole crew. Compatibly with the weather and sea conditions, it has often involved us in the choice of bays, any roadsteads or stops in port, and this is very appreciable and rare to find. The crew was made up of fantastic people who have remained in my heart, but it is also thanks to Max to have been able to create a pleasant atmosphere of fun and serenity. In addition to being a great captain for us at the end of the holiday he became a friend, he and his fantastic partner. See you next time captain! Ps: if you have doubts about Max's choice you are crazy :)
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Sailing from Corfu to Zakynthos in 7 days

08/27/2025

Alberto B.

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Italy

Max was a true captain, one of those who make you feel safe and who turn a holiday into an indelible memory! From the first day he welcomed us with a smile and with a unique professionalism, clearly explaining the basic rules for living on a boat and making us feel immediately at ease, even if for many of us it was the first experience. We sailed with him, his girlfriend and another couple for 8 days: from perfect strangers we became a close-knit group of friends, thanks also to his ability to create a serene and fun atmosphere. With Max it was not just a holiday at sea, but a real journey of discovery. He guided us through hidden bays and coves, corners of paradise that we never expected to see, giving us breathtaking scenery. The sunrise when we were lucky enough to spot a seal will remain forever in our hearts! He did not limit himself to showing us the sea: he also took us to visit the characteristic villages of each island, taking care of every detail and always leaving room for sharing, because every choice of route or activity was taken together, like a real crew. His passion for the sea, his expertise in navigation and his attention to people made this first experience on a boat something special and unforgettable. Thanks to him we experienced days full of adventure, laughter, relaxation and magic. I sincerely recommend anyone to experience the sea with Max: he is not just a skipper, but a true travel companion capable of making you fall in love with life on a boat.

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