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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.

52

experiences

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5.0

Aeolian Islands on a sailing boat, an exaggerated holiday!

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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6 travellers

Starting from

€450

Per person

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4.8

Super!

Discovering the Aeolian Islands Between Nature, Relaxation and Fun - From Palermo to Lipari

Duration:

8 days - 8 nights

Italy:

Aeolian Islands

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19 travellers

€795

Per person

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A week to discover the Aeolian Islands and the Volcanoes

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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8 travellers

€700

Per person

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4.8

ENJOY: from the Aeolian Islands to Portorosa

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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10 travellers

€790

Per person

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5.0

Aeolian Islands Sailing with the Family!

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€875

Per person

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4.7

Magical sailing crossing from Procida to the Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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3 travellers

€690

Per person

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4.9

Super!

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

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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40 travellers

Starting from

€700

Per person

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5.0

Le Eolie da Vulcano in una Barca Esclusiva

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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4 travellers

Starting from

€500

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years. - Live them with us.

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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5 travellers

€583

Per person

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Discovering the Aeolian Islands by catamaran with hostess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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34 travellers

Starting from

€1,250

Per person

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5.0

Super!

Holiday in the Aeolian Islands: comfort, adventure and music! - Chef on board

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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10 travellers

Starting from

€900

Per person

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4.8

Super!

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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23 travellers

Starting from

€1,150

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

1748 reviews

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Sea, sailing and relaxation in the beautiful Aeolian archipelago

05/4/2025

Alexia D.

-

France

Super séjour avec Antonino ! Il est très sympa, à notre écoute et très arrangeant ! On a visité les îles de Vulcano, Salina et Panarea. Le rythme était adapté à nous : on a bien pu profiter du voilier et des îles sur lesquelles on a randonné et/ou on s'est promené. Le voilier est très fonctionnel,nous avons cuisiné à bord certains jours. On s'est senti comme à la maison et avons partagé de bons moments avec Antonino. Une superbe façon de voyager : on recommande vivement !
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We have known the Aeolian Islands for 20 years. - Live them with us.

04/28/2025

Anne-Marie M.

-

United Kingdom

We had an action packed week with plenty of interesting activities for adults and children alike. The skipper is a very skilled sailor and attentive to his passengers. The boat is clean and comfortable.
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Aeolian Islands by catamaran, professional skipper/hostess, what else?

10/6/2024

Marco G.

-

Italy

Esperienza splendida! Prima volta per noi in barca - ma sicuramente non l’ultima! Super consigliata per chi vuole godersi il mare da una prospettiva diversa e con un ritmo più naturale. Andrea skipper super disponibile e di compagnia; Arianna super attenta e premurosa.
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

10/3/2024

Giovanni L.

-

Switzerland

Lo skipper Maurizio ha veramente fatto del suo meglio tenendo conto del tempo atmosferico a volte inclemente che non ci ha permesso di raggiungere tutte le mete. Un saluto particolare a Tina che è una santa donna e ha tenuto insieme con allegria e simpatia un gruppo di persone di estrazione molto diversa che si sono incontrate la prima volta sul catamarano.

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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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