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Sailboat yacht sailing holidays & tours in Aeolian Islands

Discover more than 7 opportunities to get on board a Sailboat adventure in Aeolian Islands. A unique experience with a local skipper, starting at €350 a week.

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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 Aeolian Islands

1822 reviews

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End of season weekend in the Aeolian Islands

11/3/2025

Collwyn Y.

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Italy

I come from the North Sea but I now live the Italian Alps and I’ve been really missing the ocean. So, after much thinking, I decided to treat myself to a little sailing holiday in October. [hidden] (the boat) is cozy yet has every comfort and the hosts really make you feel like you’re being treated to an Italian family gateway. Giacomo and Laura go above and beyond to fit everyone's need and requests. They exceeded my expectations! Great company, great food and insane landscapes! Nothing quite like sleeping under the stars, lulled by the gentle rocking of the boat. Thank you, I hope next time I can bring my family from Scotland!
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End of season weekend in the Aeolian Islands

11/3/2025

Gaia R.

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Italy

Honestly, I had underestimated a sailing holiday in Sicily in October but instead it was unforgettable. The Aeolian Islands are even more beautiful in this period, being less crowded. Living them from the sea, guided by two local people, then, becomes a truly authentic experience! Thank you Giacomo and Thank you Laura, we will definitely be back this summer to be able to have even more fun with the longer 🌬️ days
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End of season weekend in the Aeolian Islands

11/3/2025

Edoardo T.

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Italy

End of October, I still want summer and I decide to do a little madness... on a sailing boat to the Aeolian Islands!! I was undecided but in the end I threw myself into it and I couldn't have made a better choice. The best boat, the best crew: the company, the food... everything really great!! What can I say: I'll be back in the summer!!
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End of season weekend in the Aeolian Islands

11/3/2025

Francesco P.

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Italy

I have always dreamed of taking a sailing holiday and I treated myself to a mini-weekend in October: reality exceeded expectations! The Aeolian Islands are fantastic islands, the colors of the landscape surreal. Sturdust and his crew an excellent company. Thanks to Giacomo and Laura for their hospitality, 5 well-deserved stars on everything!

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