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Sailboat yacht sailing holidays & tours in Ionian Islands

Discover more than 5 opportunities to get on board a Sailboat adventure in Ionian Islands. A unique experience with a local skipper, starting at €350 a week.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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 Ionian Islands

841 reviews

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Gone with the Wind, Corfu and the Poseidon Islands

09/15/2025

Annamaria S.

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Italy

Nice holiday in the blue of the sky and the sea!! On the other hand, the return to the gray sky and traffic of Bergamo was challenging
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/15/2025

Claudio S.

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Italy

Unforgettable trip! Skipper and hostess were super skilled, kind and always available. Great food, stunning places, the magic of sailing and the best company on board. Couldn’t ask for more!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/14/2025

Madison T.

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Canada

Wow wow wow. We had no idea what to expect when booking this trip, it exceeded every expectation. Alessandro is knowledgeable and kind, his passion for what he does shows. Carlo is sunshine in human form, the food he makes on board is incredible. Eros is the perfect addition to the boat. We felt so well taken care of the entire time. The weather was perfect early September with it being less hot than July/aug. The rooms in the boat are comfortable but it does get hot down there to sleep, I could see a usb fan being useful for sleeping. Do not hesitate to book this trip with sailing sunset.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/14/2025

Giuseppe M.

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Italy

Francis number 1. Reliable and aware skipper!

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