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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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4.4

Enjoy the Aeolian Islands with skipper and hostess

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

July - September

Starting from

€940

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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4.0

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

€750

€675

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

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

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

15 departures available

July - November

Starting from

€433

Per person

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From La Maddalena to the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

July - August

€1,600

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

1793 reviews

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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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Magical Aeolian Islands by catamaran

07/14/2025

Ciro C.

-

Italy

Amazing skipper,, cook and boat
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Discovering the Aeolian Islands Between Nature, Relaxation and Fun

07/14/2025

davide p.

-

Italy

Excellent from all points of view. Superlative skipper

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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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