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Sailboat yacht sailing holidays & tours in Greece

Discover more than 17 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

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4.8

Super!

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€1,300

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - November

Starting from

€585

€527

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

3 departures available

October

€570

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

Starting from

€950

€570

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€570

Per person

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4.9

Super!

Sailing holiday among the wonders of the Cyclades from Athens

Greece: Cyclades

6 days - 7 nights

One departure available

September - October

€690

Per person

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4.5

New

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€890

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€890

Per person

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,645

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

2 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

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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

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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 - Sailboat yacht sailing holidays & tours in Greece

1969 reviews

Corfu between bays, taverns and myths.

09/21/2026

Mónica L.

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ES

Beautiful islands, crystal-clear water, amazing sunsets and fantastic people on board. A huge thank you to Leonore, our skipper, for being so professional, kind, always making us feel safe and relaxed. And to Hansel, our super chef, for the delicious food and for making every meal something to look forward to! They were both incredibly nice and attentive and made the whole experience feel truly special! A perfect week of sailing, swimming, exploring, great food and lots of laughs. I would do it all over again tomorrow!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/21/2026

federico b.

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IT

Beautiful holiday with a crew far beyond my expectations!

Corfu between bays, taverns and myths.

09/20/2026

Francine N.

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CH

It was our first experience and, with great pleasure, we can say that we spent a beautiful and relaxing week on a boat with Leonor and Hansel. Thanks to the experience and deep knowledge of the territory of the two captains, we discovered beautiful beaches and bays. We also had good luck with the wind which allowed us to sail very often with sails. The atmosphere on board was very nice, thanks to the nice group that was created and where everyone put a positive energy to make this adventure very pleasant. To be redone! Thank you all and.. fair winds!

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

09/20/2026

Paola E.

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IT

Francesco is a super skipper: with great experience, attentive to everyone's needs, ready to welcome requests when possible and to suggest proposals to enjoy the holiday to the fullest! Always safe, he chose the best landings to make us feel good even when the weather did not seem favorable. The destination is a succession of bays, green, azure and blue seas, picturesque villages with taverns by the sea. Clean and comfortable boat with everything you need. Highly recommended!

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