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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!

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

Greece: Ionian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€550

Per person

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4.9

Super!

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

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

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5.0

Super!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

July

€790

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

One departure available

August

€2,947

€2,800

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

Per person

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5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

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4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

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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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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5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

September - 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

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

197 reviews

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

07/7/2025

Diana U.

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Italy

Amazing experience! It was my first time on a sailing boat, and it was incredible. We visited beautiful places and beaches. Ale and Carlo are the perfect duo to sail with! Ale is professional, knows everything about sailing and the best beaches, and was always available and super friendly. Carlo was also very kind and helpful. I'm a vegetarian, and he always made something special just for me. Thank you for an unforgettable week! Hope to come back soon! :)
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/7/2025

Virginia B.

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Italy

Beautiful holiday, Andrea precise and very nice skipper made us discover wonderful places and entertained us. Another honorable mention to Marta who fed and pampered us. Mattias a real sea dog! You are missing already!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

Dario B.

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Italy

A great experience! It was not my first sailing cruise but certainly the most beautiful. Alessandro is young but competent, he knows the area and the seabed very well and, not least, he is kind and very helpful with everyone. Carlo is formidable, helpful, super sporty and cooks great! Together with his brother we created a small flotilla of two boats, and also a nice group. With them we saw the most beautiful places in the area. I was a bit skeptical about Corfu before leaving, but I had to change my mind, and from the boat it is a completely different perspective. 5 stars on everything, super deserved.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

francesco f.

What can I say.. First boat trip absolutely unforgettable. Thanks to Ale, the skipper, always attentive and available to our every need or request. Thanks to Carlo, an essential steward always with a smile on his face, as well as an excellent cook and great "suppista". And thank you both for the pleasant chats while browsing. An experience that we will certainly repeat with the same crew. Not if, but when... A greeting also to Eros, a short but intense company. See you soon!.

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