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Yacht sailing holidays & skippered tours in the Aeolian Islands

A holiday in the Aeolian Islands: Vulcano, Lipari, Salina, Panarea, Stromboli, Alicudi, and Filicudi - seven volcanic islands to be discovered by sailboat. A unique experience in which you will navigate between craters, geysers, volcanic rock rivers.

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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 - Yacht sailing holidays & skippered tours in the Aeolian Islands

2073 reviews

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Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

07/27/2026

Chiara L.

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IT

Stefano was an exceptional captain, prepared, nice and helpful. It was a super week that I recommend everyone to do.

Sailing & adventure in the Aeolian Islands

07/27/2026

Ada B.

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BE

A truly unforgettable holiday. Vittorio stood out for his great professionalism, kindness and availability, managing to make us feel always welcomed and at ease. Thanks to his experience, we discovered wonderful places and experienced days of relaxation, fun and safety. An authentic and special experience, which we will take with us with great pleasure. Absolutely recommended!
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From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

07/27/2026

Sebastian R.

Fabrizio is a very qualified and competent person in his craft, and he made us spend a wonderful week!
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/26/2026

Benedetto R.

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IT

Great skipper Captain Dario, professional and precise in the management and management of his [hidden]. It makes you feel immediately at ease in a boat equipped with every comfort. I hope to see you again soon at sea. Fair Winds 🌬️ greetings Benedict

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Guides & tips


Aeolian Islands

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Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
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Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
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