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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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4.5

Sailing holiday with maximum comfort

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

September

€700

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

9 departures available

August - October

Starting from

€607

Per person

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4.9

Rebel Islands: Ustica and Alicudi

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

€740

Per person

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4.7

Sailing to Sicily: 4 days of sea, comfort and adventure

Italy: Aeolian Islands

4 days - 4 nights

One departure available

August

€375

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

6 departures available

August - September

Starting from

€723

€650

Per person

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5.0

Aeolian Islands on a sailing boat: a tailor-made holiday with an exclusive boat

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€800

Per person

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4.6

Aeolian Islands: well-being, taste and fun

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - September

Starting from

€690

Per person - min 2 pax

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Aeolian Islands by sailboat: 6 days between volcanoes and clear waters

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€6,950

Per person

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4.9

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€950

Per person

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4.9

Aeolian Islands on a luxury sailing boat

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€700

Per person

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4.2

Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€700

€620

Per person

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Aeolian Week

Italy: Aeolian Islands

7 days - 6 nights

5 departures available

August - September

Starting from

€750

Per person

Why book a holiday with Sailsquare?

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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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

2079 reviews

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

08/3/2026

Nicola B.

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IT

It was a wonderful experience: the Aeolian Islands are a magical place, there is no doubt about it, but I believe that thanks to the skipper Stefano and the sailor Alberto, his son, any wave furrowed by Ulysses' keel can become one in turn. We were lucky, our travel companions at the end of the week became friends rather than crew. If I could, I would leave today. Thank you for everything.
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Discovering the Aeolian Islands Between Nature, Relaxation and Fun

08/2/2026

Carlotta S.

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IT

Beautiful experience, Giovanni very good, always kind and helpful. He was able to convey a great tranquility. Boat equipped with everything.
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Comfortably Aeolian Islands: Catamaran Cruise with Steward

08/2/2026

chiara p.

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IT

Wonderful experience of a week in the Aeolian Islands, all organized with care and in detail to make us live every possible experience; Angelo super helpful and nice, the wonderful boat equipped with every comfort. I also thank Giorgio so much for the impeccable skipper and Diego for a very good cook, you made us spend a wonderful week. We will definitely be back for more tours!

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

08/2/2026

Luigi B.

-

IT

Unique experience. Top landscape, top crew, top food. Nothing to add.

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Guides & tips


Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Aeolian Islands: the best travel ideas

Other travel ideas

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