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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.

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

1769 reviews

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Enjoy: in the blue painted blue of the Aeolian Islands

07/2/2025

Loris C.

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Italy

Giovanni è una persona che ha trovato nel mare la sua pace interiore ed è in grado una volta a bordo della sua barca di trasmetterti la sua passione e trasportarti attraverso la sua libertà e quiete in una navigazione confortevole tra le meraviglie della natura incontaminata . Grazie capitano.
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Aeolian Islands - A week on a sailing boat with skipper and assistant

07/1/2025

Rodolfo B.

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Italy

Vacanza praticamente perfetta, a partire dalla descrizione, dall'organizzazione, dalle informazioni dettagliate fornite prima della partenza. Anche grazie al meteo favorevole e agli ottimi compagni di viaggio, abbiamo esplorato tutte le Eolie dedicando il giusto tempo a tutto, anche a noi stessi, senza correre. Non solo, con le escursioni via terra l'esperienza è andata ben oltre le mie aspettative. Luigi ed Enrico sono persone squisite, disponibilissime, con cui è molto piacevole conversare su ogni argomento, costantemente impegnate a fare in modo che tutto proceda per il meglio. Al rientro saluto tutti con un nodo alla gola, sperando di ritrovarsi in futuro magari ancora in barca.
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Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

06/30/2025

Alessandra M.

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France

É stata un’esperienza unica, la barca é il modo migliore per visitare le bellissime Eolie. E che barca: un catamarano grande e moderno, con uno skipper esperto ed affidabile affiancato da una bravissima cuoca. L’atmosfera a bordo era perfetta, con il mix ideale di relax e divertimento. Non sono mancate escursioni a terra (trekking su Vulcano e visite ai bellissimi paesi isolani, anche solo per mangiare una granita), nuotate in luoghi segreti meravigliosi, notti in rade silenziose, serate nei locali a terra, aperitivi guardando il tramonto in mezzo al mare… davvero la vacanza perfetta per chi vuole godersi le isole.
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We have known the Aeolian Islands for 20 years, live them with us!

06/30/2025

Claudia M.

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Italy

Esperienza meravigliosa! Pasquale è molto preparato e ben organizzato. Ci siamo sentite sempre al sicuro in barca. Navigazione e paesaggi stupendi.

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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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