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Sailboat yacht sailing holidays & tours in Greece

Discover more than 23 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

23 departures available

May - October

Starting from

€1,300

€1,170

Per person

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4.9

Super!

From Kos to Samos: the perfect Dodecanese

Greece: Dodecanese

7 days - 7 nights

2 departures available

August - September

Starting from

€800

€760

Per person

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4.9

Super!

From Ios to Milos, the best of the Central Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

€800

€720

Per person

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4.9

Super!

From Kos to Kos . Between volcanic islands and blue sea

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€900

Per person

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4.9

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

€700

€630

Per person

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4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

2 departures available

August - September

Starting from

€800

€760

Per person

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4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

16 departures available

June - September

Starting from

€600

€540

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

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4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - September

Starting from

€850

€808

Per person

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4.9

Super!

From Samos to Kos – Seven days sailing among the Aegean islands

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

€900

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

33 departures available

March - October

Starting from

€490

Per person

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4.9

Super!

Between sea and pine forests, the archipelago of blue: Skiathos, Skopelos and Alonissos

Greece: Sporades

7 days - 7 nights

3 departures available

June

€850

Per person

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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

2014 reviews

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

11/3/2026

Alvise V.

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IT

Great!
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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

Francesca A.

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IT

We spent a beautiful week together with Alessandro.Even if the weather was not the most clement, we were able to visit beautiful and characteristic places that we could never have discovered in any other way. In addition to the fantastic experience itself, it was Alessandro who made the difference: an experienced captain, a true master of life, with a wealth of stories to write a book about. We spent days between the sea, the wind and its stories, eating and drinking together as old friends. Thank you Ale, we will always carry you in our hearts with the hope of meeting again soon. Francesca and Davide
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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

manuela c.

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IT

I had a great time on the boat with Ale, a professional, kind, helpful person who tried to please everyone (and it's not easy!) and super nice. I saw very beautiful places despite the islands being quite man-made, took nice baths in magnificent roadsteads and visited beautiful villages with even some trekking. Beautiful, solid and comfortable, the boat, suitable for any navigation, I have always felt safe. Ale also always available to cook for everyone! Experience to be done again next year in other islands. Thank you

The fantastic Saronic Islands and the surroundings of Athens

10/19/2026

ASLIHAN A.

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TR

Alessandro was the best captain one could ask for. I had to leave after two nights because of a health emergency back home. He offered me a free sailing trip im April.

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