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Sailboat yacht sailing holidays & tours in Greece

Discover more than 96 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

10 departures available

July - October

Starting from

€570

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

13 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

€800

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

2 departures available

August - September

Starting from

€650

€585

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

15 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

One departure available

July - August

€890

€680

Per person

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4.9

Super!

From Kos to Rhodes, the South Dodecanese on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,000

Per person - min 2 pax

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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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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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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

1802 reviews

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Corfu between bays, taverns and myths.

07/6/2026

Stefano C.

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IT

The skipper, Hansel is really very prepared. He knows the places very well; both for safe, better moorings and in moving on land. He always has stories for every place he reaches. When needed, it knows how to move with excellent results even in the kitchen. Highly recommended.

Zakynthos and the Strofades Islands: a unique route in Ionian Greece

07/5/2026

John B.

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US

This was such a great experience! Giovanni and Stefania (and Remo) are terrific hosts who balance being great guides and "friends" while also creating space for us all to have some space apart - not easy on a sailboat. Our family of four will remember this trip for a long time to come.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/5/2026

Jacopo M.

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IT

We spent an amazing week sailing with Andrea and his team. The experience was simply perfect: the boat was immaculate, the food was excellent, and Andrea showed extraordinary care for his guests. A special mention goes to the hostess, Carol, who was absolutely fantastic in taking care of us and treating us to her wonderful dishes. Thank you too, Mattias—you are a truly special soul. If we could have given it a sixth star, we would have without hesitation. Highly recommended!

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

07/5/2026

Aymeric D.

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FR

We had a wonderful week on Andrea's boat! Andrea is a very kind, professional and attentive skipper. He drove us to fabulous places and made many suggestions, he knows the area perfectly. The breakfasts and meals prepared by the hostess Carol were very good and fresh. Thank you to her for her kindness and availability. We highly recommend this experience! And a little word for Mathias, Andrea's dog, who made us laugh ❤️ a lot

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