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Yacht sailing holidays & skippered tours in Greece

Discover more than 79 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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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

4 departures available

August - September

Starting from

€1,300

€1,170

Per person

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4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

August - September

Starting from

€2,300

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

5 departures available

August - September

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

One departure available

August

Starting from

€650

€585

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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5.0

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

August - September

Starting from

€570

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

4 departures available

July - September

Starting from

€700

€665

Per person

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4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

August

Starting from

€1,450

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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4.9

Super!

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

Greece: Dodecanese

7 days - 7 nights

One departure available

August

Starting from

€1,000

Per person - min 2 pax

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 - Yacht sailing holidays & skippered tours in Greece

1925 reviews

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

06/22/2026

Elisabetta M.

Breathtaking experience, fantastic landscapes and I had the pleasure of sharing all this with special people! A special thanks to Alessandro and Carlo for their availability and professionalism! A must do.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

06/22/2026

Michela B.

-

IT

A beautiful experience shared with unknown but amiable and sociable people. We were lucky. Gianfranco, the skipper is very good and this makes navigation safe and relaxed. The Sporades are beautiful, very green and with a crystal clear sea. Super recommended.
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Catamaran with chef in the magical sea of the Ionian Islands

06/21/2026

Lorenzo G.

-

GB

We had an amazing catamaran holiday in Greece. The places we visited were absolutely stunning, with crystal-clear waters, beautiful beaches, and unforgettable scenery. The catamaran was fantastic, comfortable, well-maintained, and perfect for exploring the Greek islands. A special thank you to our skipper and hostess, who made the entire experience exceptional. Their professionalism, kindness, and attention to detail created a relaxed and enjoyable atmosphere throughout the trip. The food was delicious, and every meal was prepared with great care. Another highlight was sharing this adventure with such a wonderful international group of fellow travellers. It was a pleasure meeting people from different countries and creating great memories together. Thank you to our skipper and hostess for the excellent sailing, the wonderful cuisine, and for making this such a memorable holiday. We would highly recommend this experience and would gladly do it again.

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

06/16/2026

Liubov S.

A wonderful experience! Highly recommended!

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