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Sailboat yacht sailing holidays & tours in Ionian Islands

Discover more than 6 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

834 reviews

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

09/13/2025

Jacobus Daniel v.

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New Zealand

We had a blast! Food was great - the skipper was awesome, he really went out of his way to show us the best local spots and make the experience great. Would definitely highly recommend. Thank you so much for a great time!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/8/2025

Domenico F.

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Italy

Andrea is a very prepared skipper, he showed us beautiful places despite the bad weather made us change the itinerary a bit, he recommended a lot of typical taverns with delicious food and was always available for any kind of need. Marta did not let us miss anything, excellent breakfasts and lunches, far too helpful. There was a bad storm in Corfu on the first day and they delayed the departure by a few hours so as not to make us miss the holiday. I would say everything perfect
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From Corfu sailing between turquoise sea and white beaches - hostess on board

09/8/2025

Ignacio G.

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Spain

We are a family of 4, two kids under 12, and our experience could not have been better. Omar and Enrica are a great team that take care of you sailing and in the boat. We enjoyed beautiful locations where they made their best to arrive at times where we could be (almost) alone. They also ensured we could do nice sailing and visit beautiful locations. Also their cooking on the boat was great! healthy and delicious! Last, but not least, boat is super nice and well taken care of. We will do our best to do some more sailing and, for sure, we will call them back!! Strongly recommended as friends and/or family. Definitively worthy.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/1/2025

Cinzia S.

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Italy

I spent an unforgettable week sailing in the beautiful area of Lefkada. Breathtaking landscapes, bays with crystal clear water and sunsets that look like paintings: an experience that will remain forever in my memories. A special thanks goes to skipper Francesco, who with professionalism, passion and sympathy made the holiday even more unique. Always attentive to the needs of the whole crew, he guided us safely to discover hidden corners and made us feel at ease from the first to the last day. I recommend this experience to anyone who wants to experience the sea in freedom and relaxation, with the certainty of being in excellent hands. Thank you Captain

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