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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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The world's largest marketplace for sailing holidays

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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 - Yacht sailing holidays & skippered tours in the Aeolian Islands

2001 reviews

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A week in the Aeolian Islands - 6 islands in seven days

09/17/2025

Giuseppe I.

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Italy

The sailing trip with Nicola was an experience that enriched me a lot, unique emotions and sensations. The navigation, the wind, the sun and the sea created a perfect mix of adventure and relaxation. I recommend everyone to try this experience at least once in their life: it is an opportunity to discover the beauty of the sea, the Aeolian Islands and the feeling of freedom. Thanks to all the crew, who made all this possible.
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A week in the Aeolian Islands - 6 islands in seven days

09/17/2025

Sirio M.

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Italy

Nicola is an excellent connoisseur of the Aeolian Islands. With his experience, he always puts the safety of the crew first, adapting the tour of the islands to the weather conditions. The experience was truly complete, alternating navigation with land visits where Nicola always advised on the various possibilities. The boat is a Jeanneau Sun Odyssey 42.2 feet (12.8m) from the late 90s, kept tidy with various updates and options such as electric toilets. With full crew, 8 people, it suffers a little from confined spaces but all in the canons of a sailing holiday. The descriptive sheet of the boat faithfully reflects reality. Excellent experience of having sailed with the use of the Geannaker, a sail that also takes advantage of light winds, a nice surprise not being commonly used on charter boats, thank you!
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A week in the Aeolian Islands - 6 islands in seven days

09/17/2025

Sarah N.

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Italy

I had an unforgettable sailing holiday thanks to our skipper! Always professional, helpful and attentive to everyone's needs, he made us feel safe at all times. He was able to combine competence and sympathy, making navigation relaxing and pleasant. He took us to wonderful bays, told us curiosities and made us experience the sea in an authentic way. The Aeolian Islands are a beautiful experience that I recommend to anyone who wants to discover sailing with the guidance of a reliable and passionate skipper. Thank you Nicola!!
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A week in the Aeolian Islands - 6 islands in seven days

09/15/2025

Ilaria I.

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Italy

Top experience! Nicola, the skipper, is nice and super reliable, he took us to magnificent places, he was understanding to put up with us all, always available even with the kitchen, but never intrusive, and proposed an itinerary based on the weather that allowed us to see 6 islands, and allowing those who wanted to disembark on land and take turns in the village, or stay on the boat for those who, like me, prefer to enjoy the beauty of the roadstead. Very beautiful and spacious boat, as much as a sailboat can be, equipped with many small modernity and comforts. Even the group that was created with the other participants was beautiful and cohesive, leaving everyone their own freedoms. The journey to reach the Aeolian Islands and to return, starting from Livorno, was not the easiest and most direct, but it was really worth it, so don't be discouraged but leave and choose Nicola, a man of the sea and experience, and you will feel "safe". What to add if not one I hope "see you soon!" Thank you Nicola and your [hidden]!

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