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Crewed yacht sailing holidays & tours in Greece

Get on board on a crewed sailing holiday in Greece for the most relaxed time ever.

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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

4 departures available

September - November

Starting from

€550

Per person

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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

5 departures available

September - October

Starting from

€1,100

€880

Per person

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4.8

Super!

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

Starting from

€2,100

€1,995

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!

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

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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

One departure available

October

€550

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

Starting from

€1,260

Per person - min 2 pax

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4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€835

€752

Per person - min 2 pax

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Unique Cyclades sailing holiday with Hostess

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

€994

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 - Crewed yacht sailing holidays & tours in Greece

239 reviews

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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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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/14/2025

Madison T.

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Canada

Wow wow wow. We had no idea what to expect when booking this trip, it exceeded every expectation. Alessandro is knowledgeable and kind, his passion for what he does shows. Carlo is sunshine in human form, the food he makes on board is incredible. Eros is the perfect addition to the boat. We felt so well taken care of the entire time. The weather was perfect early September with it being less hot than July/aug. The rooms in the boat are comfortable but it does get hot down there to sleep, I could see a usb fan being useful for sleeping. Do not hesitate to book this trip with sailing sunset.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/14/2025

Maude A.

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Canada

Wonderful week with Alessandro and Carlo! We ate well and saw beautiful places. Carlo is an angel, always ready to help. Alessandro is an extraordinary skipper. He knows how to make us feel confident and safe. He too is always ready to help. The boat is beautiful. The activities were fun and the pace of the activities was good. We were also happy to be able to sail when the wind allowed. We also had a great week with the new people we met on the boat. I 100% recommend this cruise!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/14/2025

Janine W.

-

Switzerland

It was perfect. Great crew. Beautiful destinations. We would definitely recommend it.

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