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Sailboat yacht sailing holidays & tours in Greece

Discover more than 91 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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - 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

12 departures available

August - 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

One departure available

August

€800

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

14 departures available

July - November

Starting from

€700

€665

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

September

€650

€585

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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4.9

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

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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

1807 reviews

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

07/12/2026

maddalena d.

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IT

Alessandro has greatly contributed to making this holiday special. He is a very good skipper, he transmits safety and reliability but above all he is an interesting, nice and fun person. Great chef... He delighted us with yummy dishes and great entertainer. I hope to be back soon on board [hidden]:) see you soon Madda and Valerio (Vittorio/vincenzo).

Corfu between bays, taverns and myths.

07/11/2026

Stefania A.

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IT

Beautiful holiday, definitely to be redone! Very knowledgeable and welcoming crew Great cooks... (which doesn't hurt) All positive

Corfu between bays, taverns and myths.

07/9/2026

Loredana L.

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IT

Beautiful experience! Hansel, in addition to being a great captain, is also hospitable and attentive to every detail to make you experience a real holiday! She treated us like princesses, making us spend wonderful days in beautiful places and in total relaxation! Then I cannot fail to mention his skills as a great Chef! A truly special touch to everything was then given by our captain Leonor!!! super super super good, sweet and nice!
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Corfu between bays, taverns and myths.

07/8/2026

Farida B.

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IT

Fantastic experience! Traveling on a sailing boat is always a wonderful experience, if you do it with two captains like Léonore and Hansel, always professional, kind, helpful, attentive to safety and excellent cooks... becomes super awesome! They took us to discover wonderful bays and hidden corners, making us feel safe at all times. A journey dedicated to the sea, relaxation and good company that I will carry in my heart. Highly recommended!

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