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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

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 - Yacht sailing holidays & skippered tours in the Aeolian Islands

2002 reviews

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Summer is made for the Aeolian Islands! Weekly cruise

09/18/2025

Jurij P.

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Italy

Nothing to complain about the Skipper, the destination and the boat... Since Davide, proved to be a person with great experience very attentive to the needs of each participant in the experience... And even his boat, which I had chosen because it was equipped with a bathroom for each cabin, proved to be what was expected... The same thing is the itinerary which of course can also depend on the weather accounts, which Davide has been able to manage very well ... Unfortunately, however, this time the sore point is related to the fact that I was able to see a huge flaw not in the boat but in what is the transparency policy of this site ... Unfortunately, in fact, sure that I have PURPOSELY booked an experience with all my peers - upon arrival I discover that unlike what had prompted me to make the reservation with this search engine wandering € 150 more than the other participants all ... In addition to the insurance another € 90 - on arrival then at boarding I discover that unlike this there were four over sixty years old ... As well as two girls about 20 years younger than me... This situation, even if I was able to meet and discover people of great depth and moral qualities, was not at all relevant to what I believed to be the holiday really booked... And this is simply because, with people of more or less twenty years of difference, life habits and therefore also those of a holiday, can result in diametrically opposed needs in terms of schedules and style of holiday... This I repeat Without taking anything away from the goodness of the people I know... I AM THEREFORE SORRY TO HAVE TO REVIEW THIS EXPERIENCE IN A VERY NEGATIVE WAY BECAUSE IN MY OPINION IT IS THE PORTAL OR THE ENGINE RESPONSIBLE FOR THE LACK OF TRANSPARENCY THAT INSTEAD DE' SINGS SO MUCH ON ITS SITE PRECISELY BECAUSE OF ITS AGE. FROM NOW ON AND ESPECIALLY IF THIS POLICY IS NOT REALLY CORRECTED, I WILL DO LIKE MANY BY LOOKING FOR AND CONTACTING THE SKIPPERS DIRECTLY, SINCE I WAS NOT AT ALL SATISFIED WITH THE POLICY OF TRANSPARENCY FEARED BUT NOT REALLY PRACTICED. It should therefore be noted that although I gave full marks to both Skipper Davide and the destination as well as his boat, the overall grade of the experience can only be at a minimum due only to the lack of IMPLEMENTATION of transparency, FEARED on this portal. You are curious whether or not this will be published and made available for reading by all greetings without thanks. Yuri
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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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