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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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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€751

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€935

€748

Per person

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4.9

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September

Starting from

€583

€525

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

11 departures available

July - October

Starting from

€530

€504

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

August - September

Starting from

€689

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - November

Starting from

€650

€585

Per person

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4.8

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

7 departures available

August - October

€590

Per person

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4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€640

Per person

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4.8

Super!

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€910

€819

Per person - min 2 pax

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4.9

Aeolian Islands on a luxury sailing boat

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

July - August

Starting from

€700

€500

Per person

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4.8

Super!

Discovering the Aeolian islands: nature, relaxation and fun

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€745

€671

Per person

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5.0

Super!

Aeolian Islands - Volcanoes, Sail & Trekking - Mountain Guide on board

Italy: Aeolian Islands

5 days - 6 nights

One departure available

August

€1,430

€1,287

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

1777 reviews

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Between seas and volcanoes, fall in love with the Aeolian Islands

07/8/2025

Marco C.

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Italy

There are journeys that remain in the skin like salt after a long swim. Our experience in the Aeolian Islands, 8 friends on a sailing boat with Antonio was just that: an immersion in beauty, quiet and authenticity. The boat, kept with care and love, was our floating refuge, from which new explorations departed every day. The beaches and coasts that Antonio was able to make us discover were hidden and never banal corners, where time seemed to dilate. The long exploratory swims between wild coves, transparent seabeds and rocks sculpted by the wind will remain among the most vivid and intense memories. Even on land, each stage was a small enchantment: tastefully selected restaurants, authentic and atmospheric places, simple and true flavors like the sea that lulled us. Antonio was not only our skipper, but a travel companion capable of becoming part of the group naturally. With his calm, his sympathy and that serenity that seems to come directly from the sea, he made this experience unique, true, full of harmony. A holiday that has the flavor of wind, freedom and beautiful things that are not forgotten. Thank you Antonio, you have given us a holiday that we will carry in our hearts.
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We circumnavigate the Aeolian Islands starting from Vulcano

07/8/2025

Federica R.

-

Italy

With Alice and [hidden] you can live the real experience of a boat holiday! Very nice places to relax, peace and nature!
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Aeolian Islands: between sea and authentic flavours

07/7/2025

Achille V.

-

Italy

We had an unforgettable experience in enchanting places. Also thanks to the competence and sympathy of Emiliano and Nila.
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/7/2025

Elisa S.

-

Spain

Dario was an exceptional captain! Attentive, helpful, wise and prudent. Perfect organization and itinerary. Priceless advice from a true local. The boat is kept like a jewel. Comfortable, clean, tidy and bien organized. Thanks to Dario and the rest of the crew for this wonderful holiday

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