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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

experiences

4.8

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

5 days - 6 nights

One departure available

September

€1,995

Per person

4.6

Una vera navigazione con uno skipper oceanico

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

€750

Per person

5.0

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

September - October

€990

Per person

Unique Cyclades sailing holiday with Hostess

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

€994

€795

Per person

Tour by schooner to discover Antiparos - Despotiko - Blue Lagoon

Greece: Cyclades

1 day - 0 nights

29 departures available

September - October

Starting from

€115

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.

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

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

1884 reviews

From Samos to North Dodecanese Kalymnos on a magnificent 15-meter boat

09/16/2025

Bruno P.

We had a great time aboard the Alizé! As the other passengers have already indicated, Fabio and Irene, thanks to their professionalism, their kindness, their attention to detail and also (this is important! :)) their delicious dishes, allowed us to enjoy a week of happy disconnection. They quickly understood what we liked (fishing, sailing, hiking and discovering the beautiful Greek islands) and adapted the program accordingly. For us, we didn't spend a week with two strangers, but with friends. See you next year!

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

09/15/2025

Florian H.

Germany

Great trip & great skipper!

Gone with the Wind, Corfu and the Poseidon Islands

09/15/2025

Annamaria S.

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

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

09/15/2025

Claudio S.

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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