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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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Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

August - September

Starting from

€700

Per person

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5.0

Eolie autentiche in barca a vela: tra sapori locali e mare cristallino

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August

€850

Per person

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4.8

ENJOY: from the Aeolian Islands to Portorosa

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€720

Per person

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4.0

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

13 departures available

July - October

Starting from

€625

Per person

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4.9

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€870

Per person

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4.6

Discovering the Aeolian Islands

Italy: Aeolian Islands

7 days - 6 nights

5 departures available

July - August

Starting from

€780

€702

Per person

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4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€950

€760

Per person

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5.0

Discovering the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€820

Per person

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4.0

15 days wandering in the southern Tyrrhenian Sea

Italy: Aeolian Islands

15 days - 15 nights

One departure available

August

€1,950

€1,755

Per person

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3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

12 departures available

July - November

Starting from

€600

Per person

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5.0

Aeolian Islands in style! Only for four

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

July - August

Starting from

€1,125

Per person

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4.5

Sailing holiday with maximum comfort

Italy: Aeolian Islands

6 days - 7 nights

13 departures available

July - November

Starting from

€720

Per person

Why book a holiday with Sailsquare?

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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

1795 reviews

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

07/18/2025

Dag Petter H.

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Norway

Seven days of pure magic in the Aeolian Islands – an unforgettable experience thanks to Nicola We have just finished a week on a sailing boat among the beautiful Aeolian Islands and we cannot find the words to describe how extraordinary this experience was. The credit for this perfect trip goes above all to our skipper, Nicola, an impeccable, experienced and passionate guide, who turned every day into something special. From the first moment on board, Nicola made us feel safe and comfortable. His knowledge of the sea, the islands and the winds is impressive: he took us to hidden coves and dreamy bays, away from the most crowded tourist routes, making us experience the most authentic and wild Aeolian Islands. He was able to read the weather and adapt the itinerary with intelligence and flexibility, always ensuring maximum comfort and beauty. In addition to being an excellent skipper, Nicola is a sunny, hilarious, kind and always helpful person. He was able to create a relaxed and convivial atmosphere on board, bringing the group together naturally and making every moment – from sailing at sunset to aperitifs at anchor – unique and unforgettable. The nights under the stars, the crystal clear water of Panarea, the fumaroles of Vulcano and the fiery sunsets seen from Filicudi deserve a separate chapter... each island gave us different emotions, but all with a common denominator: the feeling of being in excellent hands thanks to Nicola. If you are thinking of a sailing holiday in the Aeolian Islands, do it – and if you can, choose Nicola as your skipper. He is not only an experienced captain, he is a true lover of the sea who will make you experience the islands with new eyes. Thank you very much, Nicola, from Greta and Petter. See you on the next adventure!
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ENJOY: in the blue painted blue of the Aeolian Islands

07/17/2025

Ellis M.

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Germany

A fantastic experience and trip, thanks to the wonderful skipper/chef Matteo!
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We have known the Aeolian Islands for 20 years, live them with us!

07/15/2025

Arianna O.

Pasquale made this holiday even more memorable and wonderful!
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Eolie autentiche in barca a vela: tra sapori locali e mare cristallino

07/14/2025

Manuela V.

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Italy

Emanuele moves around the Aeolian Islands as I slap around the house. Sailor, cook and MacGyver, he combines the experience of someone who goes to sea even before walking with the freshness of a young professional who loves what he does. Son of art, he knows and takes charge of the work behind the scenes so that his guests enjoy a relaxed, light and carefree holiday experience.

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