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Sailboat yacht sailing holidays & tours in Greece

Discover more than 101 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

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

11 departures available

July - October

Starting from

€1,200

€1,080

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,110

€999

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

12 departures available

July - October

Starting from

€570

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€650

€585

Per person

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5.0

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

Greece: Ionian Islands

7 days - 7 nights

15 departures available

July - October

Starting from

€570

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

2 departures available

August

Starting from

€800

€720

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

16 departures available

July - November

Starting from

€700

€665

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

2 departures available

July - September

Starting from

€890

€680

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

5 departures available

July - October

Starting from

€600

€540

Per person

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4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.9

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

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 - Sailboat yacht sailing holidays & tours in Greece

1794 reviews

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Sporades Experience: Freedom, Turquoise Sea and Greek Magic

06/28/2026

Raffaele S.

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IT

I have taken several sailing holidays, some of them with Sailsquare. Gianfranco is certainly a man of the sea. Unfortunately, my experience was not positive. The atmosphere on board has always been very tense, linked to the fact that it makes you feel like you are an (unwanted) guest in his home. On several occasions he addressed other members of the group in a rude and rude way, if not to me. In a week he has never used the tender nor allowed anyone to use it. Finally, I did not find the economic requests transparent: on the site a sum of 50 euros is specified as a starter pack (in addition to the common fund) while the day before leaving he sent a sort of personal vademecum in which he requested a total of 500 euros from the 8 participants, as well as requesting, before returning to port, an additional 50 euros. Ultimately, beyond the economic aspect which is not very relevant to me, I did not spend a relaxing week off work but in a very heavy and negative climate. I am very respectful of others and it would be correct to receive the same... especially if they pay you.

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

06/28/2026

Jonathon M.

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IE

Francesco was a brilliant skipper. He gave us the best experience, brought us to so many amazing spots and was really welcoming and friendly. Highly recommend booking a sail trip on his boat
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/27/2026

Viviana M.

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IT

Super week!! Fantastic sea, wonderful beaches with crystal clear waters and delicious cuisine. Alessandro, skipper and Carlo, were very kind and company! My sister and I spent a relaxing and fun week together with the group who traveled with us and we made friends with. Recommended for people who love the sea, the wind in their hair and need lightness, simplicity and freedom! Thank you for this great week!

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

06/24/2026

Cesare S.

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IT

Annalisa and Emanuel were fantastic hosts! They made us sail and cooked us excellent meals making us spend a beautiful week discovering the sea of the Cyclades and its beautiful bays, despite the Meltemi

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