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Family sailing cruises yacht sailing holidays & tours in Aeolian Islands

Discover more than 2 opportunities to get on board a Family sailing cruises 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

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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 - Family sailing cruises yacht sailing holidays & tours in Aeolian Islands

60 reviews

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Aeolian Islands - A week on a sailing boat with skipper and assistant

09/8/2025

Maruscka D.

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Italy

One word to describe this experience, wonder! Luigi's indisputable experience and Enrico's irreplaceable attention made the week on board the boat [hidden] a pleasure for all our senses: our eyes full of breathtaking landscapes and the unique colors of beaches and skies in all their shades; our palate delighted by the expertly prepared dishes for a tasty discovery of the local cuisine; the stories of the islands during navigation and the sound of the sea transformed into a pleasant symphony for our ears; the scents of the Sicilian land among flowers, high quality ingredients and salt on the skin and last but not least the magical touch of the waters of the Mediterranean Sea and the warm rays of sunshine after a regenerating bath. Thank you so much from me and my little travel companion who will forever carry with her the memory of an exciting journey, thanks to two people with a big heart and capable of transmitting their unconditional love for the sea and for life. Good winds and calm seas! A special greeting from Maruscka and Alma
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

09/4/2025

Federica R.

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Italy

The week spent on the boat with Dario was really a wonderful experience. Dario is a precious commander! A lot Prepared, patient and attentive to the needs of the Crew needs! We had a great time with everyone, the crew was really great! We had a great time The boat is clean and very equipped! He took us to beautiful places that are hard to forget If we ever return to the Aeolian Islands we know firmly who to contact! Thank you again for the wonderful week!
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

09/1/2025

Melania C.

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Italy

More than positive experience, Dario attentive and kind skipper, it was a pleasure to travel with him. Clean and well organized boat. Aeolian Islands as enchanting as always 😊
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

09/1/2025

Alessandra L.

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Italy

Beautiful experience, made even more beautiful by our captain Dario and his welcome on his boat! The boat was hyper clean and cozy. and Dario has managed to organize the stages in the various islands and in the beautiful coves impeccably, also based on the weather, which at the end of August can vary unexpectedly. Dario is an excellent captain, who managed to meet all our needs with courtesy, professionalism and aimpathy!! A holiday that I recommend to everyone!

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