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Yacht sailing holidays & skippered tours in Greece

Discover more than 22 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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5.0

Super!

Ionian Greece aboard a Catamaran with Skipper/Chef

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,900

Per person

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4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

July - August

Starting from

€1,800

€1,440

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

Per person

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4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

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5.0

Super!

Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

One departure available

July - August

Starting from

€1,099

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

July - August

Starting from

€1,000

Per person - min 2 pax

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

July

Starting from

€600

€540

Per person

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4.4

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

July - August

Starting from

€1,305

€1,109

Per person - min 2 pax

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4.9

Luxury Gulet in Northern Ionian Greece with Crew

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

Starting from

€2,650

€2,518

Per person

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4.4

Sailing from the magnificent Peloponnese to beautiful Zakynthos and Kefalonia

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€660

Per person

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

One departure available

July - August

Starting from

€845

€761

Per person - min 2 pax

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

Starting from

€1,200

Per person

Why book a holiday with Sailsquare?

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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.

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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

1962 reviews

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

07/21/2026

Giulio M.

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IT

My wife and I have just spent an unforgettable week in the Sporades islands on a beautiful, extremely comfortable and welcoming sailboat. Skipper Gianfranco proved to be an exemplary professional, very prepared and always attentive to everyone's safety. Thanks to his knowledge of the area, he took us to coves sheltered from the wind, making us discover real corners of paradise In addition to his technical skills, he was able to create, right from the start, a relaxed and fun atmosphere on board; He has always been very helpful in explaining sailing techniques, advising things to see on land, showing us the best places to taste local delicacies or simply having a chat in front of a sunset. A big thank you to Gianfranco.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/20/2026

Andrea C.

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IT

Andrea is very organized and precise. Perfect I would say for a holiday with friends

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

07/20/2026

Katia M.

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FR

Thank you to Alessandro and Carlo for a wonderful week. Tutto benissimo. It was also very pleasant to sail not far from his brother Andrea. Very good atmosphere. To be done again.
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Discovering the wild Peloponnese

07/20/2026

Carmen C.

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IT

It is impossible to be objective because it is as if I had been on a boat with my uncle (apart from payment) so familiar was the climate. An uncle is not judged, he is taken for what he is, strengths and weaknesses. I can only say that I was fine.

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