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Sailboat yacht sailing holidays & tours in Greece

Discover more than 65 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

7 departures available

August - 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

9 departures available

August - October

Starting from

€570

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

12 departures available

August - November

Starting from

€700

€665

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!

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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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

One departure available

September

€990

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

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4.8

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

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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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

1855 reviews

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Whale watching cruise with WWF guide in the Corfu archipelago

08/3/2026

Carlo P.

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NL

It was what I wanted
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/3/2026

Francesco G.

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IT

We participated in this week on a sailing boat and we can only be fully satisfied with how it went. Alessandro the skipper and owner is always attentive to the needs of the guests and to the details, ensuring an organization of the timing that allows you to see a lot of beaches and bays at the most suitable times. Practically always we happened to be among the first in the various bays and roadsteads to have an optimal position, considering that we were at the end of July and there was a large amount of boats and tourists everywhere. Carlo the steward is always available and accomplice in on-board and "sporting" activities such as long swims in company or on the SUP. The third member of the crew was the sweet Eros, a sailor dog who always accompanied us without ever getting in the way. Added value to the package is the presence of the second boat of Alessandro's brother, Andrea. We were able to share activities and... the inevitable volleyball game in a shoal, a really fun experience! The boat was clean and welcoming, too bad we couldn't sail due to little wind that week.

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

08/3/2026

Luciana L.

Perfection! Cleanliness, professionalism, friendliness, hospitality, quality of breakfast and lunch to be eaten on board... I would spend hours praising a holiday that turned out to be extraordinary! Andrea, wonderful skipper, and his sweet and impeccable Hostess Carol will make you feel at home and experience unique moments! Thanks for everything guys! You are fantastic!

Whale watching cruise with WWF guide in the Corfu archipelago

08/3/2026

Anna C.

-

IT

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