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Yacht sailing holidays & skippered tours in Greece

Discover more than 20 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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€550

Per person

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5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

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

One departure available

September - October

€750

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.8

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€790

€711

Per person

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4.8

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

2 departures available

September - October

Starting from

€1,100

€880

Per person

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5.0

Super!

Paros-Naxos and Small Cyclades

Greece: Cyclades

5 days - 5 nights

One departure available

September

€900

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

€1,080

Per person

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5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

9 days - 9 nights

One departure available

September

€1,350

Per person

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4.0

Sailing the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

Starting from

€789

€710

Per person

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Sailing in the Saronic Archipelago

Greece: Saronic Islands and Athens area

6 days - 7 nights

One departure available

September - October

€700

Per person

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4.8

Magical Week of Wellness Yoga, Cooking, Health, and Relaxation

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,200

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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

1883 reviews

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Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

09/15/2025

Florian H.

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Germany

Great trip & great skipper!
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Gone with the Wind, Corfu and the Poseidon Islands

09/15/2025

Annamaria S.

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Italy

Nice holiday in the blue of the sky and the sea!! On the other hand, the return to the gray sky and traffic of Bergamo was challenging
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/15/2025

Claudio S.

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Italy

Unforgettable trip! Skipper and hostess were super skilled, kind and always available. Great food, stunning places, the magic of sailing and the best company on board. Couldn’t ask for more!
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Sailing holiday with yoga and SUP in the Saronic islands

09/15/2025

Nina S.

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Finland

Awesome week at sea. Elias knows all the best places to go to. It was just amazing to have this possibility to enjoy yoga, sailing, swimming, Greek food & culture in a relaxing & safe way with good company. I would definetily like to do this soon again.

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