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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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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€750

€675

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

€690

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€700

Per person

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4.9

Aeolian Islands in a big and new catamaran: sea, sun, relaxation

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€980

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

3 departures available

September - October

Starting from

€607

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

4 departures available

October

€320

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

7 departures available

September - November

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

One departure available

September

€800

Per person

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4.7

Aeolian Islands: well-being, taste and fun

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€690

Per person - min 2 pax

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

2266 reviews

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

09/17/2026

Francesco R.

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IT

Beautiful boat experience! Skipper and steward very helpful, nice and always attentive to everyone's needs. Great food, with great care also in the management of food allergies and intolerances. We felt really pampered and comfortable throughout the holiday. An experience definitely to be repeated!

Aeolian Islands: between sea and authentic flavours

09/14/2026

Anna B.

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IT

Overall more than positive experience
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Aeolian Islands on a catamaran, professional skipper/hostess, what else?

09/14/2026

Andrea D.

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IT

Simply wonderful 💙

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/14/2026

Simona L.

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IT

Wonderful holiday super recommended even for those approaching boating for the first time. The catamaran in excellent condition and comfortable for all guests, no one got in the way. The skipper Umbo proved to be competent, participatory and satisfied all our requests, he made our holiday with his sympathy, splendid and memorable! The hostess Moni' awarded for her availability 24 hours a day to all our requests, the seriousness in person, with a touch of irony that never hurt, always discreet. We also owe a special credit to the wonderful and affectionate gigi' that we loved all week. I can't quantify a vote, because it was the best holiday ever😘thank you thank you thank you Simona and Pasquale

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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

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