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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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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

2123 reviews

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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/16/2026

Olivia C.

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US

We had the best week with Capitano! He took us to the most beautiful places! The trip was a 10/10! No notes! You will not be disappointed if you book with him! Hope to sail with him again someday! :)
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/15/2026

AnnMarie S.

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US

Amazing vacation! I would compare it to somewhere between camping and glamping, but on the sea! We saw the most beautiful beaches, sunsets, and sunrises. We sailed along side dolphins, explored caves, and even saw sea urchins and octopus when we were snorkeling. Caroline was our chef an overall caretaker. She catered to our every need and the best meals we had all week were the breakfasts and lunches that she cooked for us! The boat fits up to six guests. Two of the three rooms are extremely small so if you go with friends, you will be sleeping in the same bed since there is only one bed per room. There is also no indoor shower. You shower in your bathing suit out in the open on the back of the boat. I would highly recommend privatizing the boat if you go with a group of friends. We thought we had done so, but then we found out at the last minute that there was miscommunication and a man was joining us four girls. He was very nice, but we would’ve preferred to only have one girl per small room versus doubling up and having to share space/a bathroom with a man. Overall it was a fabulous experience and I would most definitely do it again!
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

09/14/2026

Evi (Paraskevi) P.

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GR

[hidden] is a wonderful classy and spacious boat very well maintained so makes you feel safe and i couldn't get enough of the sunbathing on the lounge mattress on the bow of the boat. Captain Alessio is a down to earth,kind and calm person making this an Ideal combination for enjoying some relaxing holidays. Plus he has a lot's of knowledge around various subjects so it's really enjoyable talking to him. He made sure ,during our whole week in the Argosaronic gulf, to find for us the best anchorage with crystal clear waters. As i was the only person on board not speaking Italian captain Alessio and the rest of the crew never left me outside a conversation and always either translating or communicating in English.. Had a fantastic relaxing time, the chance to discover some sight seeing on the area make new friends and explore the local food culture. Thank You Captain.
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

09/14/2026

Lorenzo G.

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GB

A really enjoyable sailing holiday and a great way to discover the Saronic Islands. The trip offered a good mix of sailing, relaxing, and visiting interesting places, including destinations with plenty of cultural and historical interest. The boat was very well maintained and well equipped, so life on board was comfortable and easy. We had good food, good company and a very pleasant atmosphere throughout the trip. There were also plenty of opportunities to get involved in the sailing, which I particularly enjoyed. The skipper was friendly, easy-going, and always helpful, which made the whole experience very enjoyable. A very good holiday overall, and one I would happily recommend.

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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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