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Sailboat yacht sailing holidays & tours in Greece

Discover more than 49 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

9 departures available

August - October

Starting from

€1,300

€1,040

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

5 departures available

September - October

Starting from

€570

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

8 departures available

August - October

Starting from

€570

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

5 departures available

September - November

€585

€527

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

11 departures available

August - November

Starting from

€700

€665

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

One departure available

September

€650

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€600

€540

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

September - October

Starting from

€950

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

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

August

€1,200

Per person - min 2 pax

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€750

€713

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 - Sailboat yacht sailing holidays & tours in Greece

1861 reviews

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

08/10/2026

Caroline B.

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FR

The whole team was so nice. Great boat, skipper, crew, little dog Matthias ❤️ Good balance of activities and relaxation. Very pretty area. I would have changed the program of the last day of Friday which was a bit of a bit of a bit but that doesn't call into question the very high quality of the trip. It was really great!!
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Whale watching cruise with WWF guide in the Corfu archipelago

08/10/2026

Marco C.

-

IT

It was a fantastic experience. Very nice. WWF skipper and guide simply wonderful. Certainly to be repeated. Thank you Thank you Thank you
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Sailing paradise in Greece on a big 50 ft boat: the best local experience

08/9/2026

Sofia Z.

-

BE

Great sailing and holiday experience with amazing skipper and hostess.

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

08/9/2026

Gloria G.

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IT

As a first sailing experience, everything was perfect exceeding expectations. Frank was an excellent skipper, he welcomed us on his boat with extreme professionalism and sympathy, he knew how to listen to our needs and made us discover wonderful places. We highly recommend this experience. fair winds!

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