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Private yacht sailing holidays with skipper in the Aeolian Islands

Discover the magic of sailing holidays in the Aeolian Islands! Hire a whole boat: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

10 departures available

July - November

Starting from

€530

€477

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€935

€748

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - November

Starting from

€650

€585

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

12 departures available

July - October

Starting from

€530

€504

Per person

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4.8

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

8 departures available

July - October

€590

Per person

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4.8

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€910

€774

Per person - min 2 pax

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4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€640

Per person

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4.9

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

9 departures available

July - October

Starting from

€751

Per person

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4.8

Super!

Discovering the Aeolian islands: nature, relaxation and fun

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€745

€671

Per person

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5.0

Super!

Aeolian Islands - Volcanoes, Sail & Trekking - Mountain Guide on board

Italy: Aeolian Islands

5 days - 6 nights

One departure available

August

€1,430

€1,287

Per person

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4.9

Super!

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

July - September

Starting from

€870

Per person

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4.9

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Italy: Aeolian Islands

7 days - 7 nights

One departure available

July - August

€2,625

€1,940

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 - Private yacht sailing holidays with skipper in the Aeolian Islands

264 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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Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

06/30/2025

Damien D.

Amazing sailing trip. The itinerary was great, the Skipper super nice and the boat very comfortable. excellent stewardess and the food on board was delicious. we are looking forward for the next trip with Maurizio !

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