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Sailboat yacht sailing holidays & tours in Greece

Discover more than 110 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

€1,300

€1,170

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

13 departures available

June - 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

5 departures available

July - September

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

16 departures available

June - October

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

17 departures available

June - 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

€750

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - 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

1787 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.

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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.

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

06/16/2026

Liubov S.

A wonderful experience! Highly recommended!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/16/2026

Tomas F.

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GB

No No No !!!! :(. I want more. This 7 days with Allesandro ( Skipper) and Carlo (Host) was Amazing. They will take you to the best places around Corfu. Paxos and Antipaxos are paradise. Fantastic food during sailing, healthy and everyday different. We even catch big fish during sailing, and next day bee served for lunch by Fantastic Carlo. I could write review for 100 pages, but you have to explore this wonderful trip. Greetings also for Chiara, Catarina and Luca.

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