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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

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The world's largest marketplace for sailing holidays

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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

1899 reviews

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

10/1/2025

Arina R.

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Spain

It was an unforgettable journey 🤩 I totally recommend it to everyone. Andrea is very professional skipper with a lot of experience, he takes care about safety of the guests and carefully plan the route. And the most important he is an awesome person to have great conversation with. We learned so much about the sailing during the week. The hostess Marta is very kind and cooks delicious lunch. It was so comfortable that we don’t have to worry about what to eat for the breakfast or the lunch, everything was prepared by her. We visited incredible bays, had so much swim and slept under the stars sky in the sea, nothing else to ask for. But the special mentioning is to their dog Matthias, real marine dog who stole our hearts ❤️ During raining winter days I will think about Matthias that he is sailing somewhere in the Mediterranean Sea and smile! We will be missing this week, but for sure one day we will come back!

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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

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