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Yacht sailing holidays & skippered tours in Greece

Discover more than 25 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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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

Starting from

€1,300

€1,040

Per person

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4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

Starting from

€2,350

€1,880

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

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

4 departures available

October

Starting from

€570

Per person

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4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

4 departures available

September - November

€1,000

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

5 departures available

September - November

Starting from

€700

€665

Per person

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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

October

Starting from

€750

€713

Per person

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5.0

Super!

Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

5 departures available

September - November

Starting from

€1,099

Per person

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4.9

Super!

100% female sailing cruises

Greece: Cyclades

7 days - 7 nights

One departure available

October

€990

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

Per person

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4.8

Super!

Luxury catamaran cruises in the Greek islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

October - November

€1,000

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

2001 reviews

Sailing cruise in the Greek islands - The Saronic Islands

08/5/2026

Donatella M.

-

IT

The sea, the sun, the wind are nothing without a good captain and Periklis has proven to be one in all circumstances and above all human expectations.
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Whale watching cruise with WWF guide in the Corfu archipelago

08/3/2026

Carlo P.

-

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.

-

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!

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