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Sailboat yacht sailing holidays & tours in Aeolian Islands

Discover more than 46 opportunities to get on board a Sailboat adventure in Aeolian Islands. A unique experience with a local skipper, starting at €350 a week.

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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

5 departures available

June - September

Starting from

€935

€748

Per person

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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

12 departures available

June - November

Starting from

€530

€477

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

June - November

Starting from

€650

€585

Per person

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5.0

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

Italy: Aeolian Islands

5 days - 4 nights

11 departures available

July - October

€590

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

June - September

Starting from

€689

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

16 departures available

June - October

Starting from

€530

€504

Per person

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4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - September

Starting from

€640

Per person

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4.8

Super!

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€745

€671

Per person

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4.8

Enjoy: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

9 departures available

June - October

Starting from

€530

€504

Per person

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4.8

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

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - August

Starting from

€910

€774

Per person - min 2 pax

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4.9

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

June - August

Starting from

€750

Per person

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5.0

Super!

Vacanza alle isole Eolie: comfort, avventura e musica! - Cuoco a bordo

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

July - August

Starting from

€900

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 - Sailboat yacht sailing holidays & tours in Aeolian Islands

1571 reviews

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

06/9/2025

Alice M.

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Italy

Settimana alle Eolie con Pasquale: vela, aperitivi e “bagni di sale” . Abbiamo trascorso una settimana in barca a vela alle Isole Eolie con Pasquale, e l’esperienza è stata tanto rilassante quanto divertente. Eravamo solo in tre a bordo, il che ha reso il viaggio intimo, personale e davvero “su misura”. Indimenticabili il tramonto su Vulcano e la spettacolare sciara di fuoco dello Stromboli che abbiamo potuto ammirare in silenzio. Pasquale è un navigatore esperto e appassionato capace di guidarci con discrezione e competenza verso angoli nascosti e affascinanti. A bordo la convivenza è stata semplice e naturale: libere di goderci la barca, partecipare alla navigazione se volevamo, o semplicemente oziare tra un bagno e un aperitivo. Ognuno ha fatto la sua parte, tra cucina e pulizie, con leggerezza e spirito collaborativo e di condivisione. Sicuramente un viaggio da consigliare a chi ricerca un’esperienza di mare autentica! PS: Un abbraccio speciale al nostro compagno di bordo Pietro — esperto di mare e, soprattutto, di vita! — Alice & Alessandra
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Long weekend exploring the Aeolian Islands

06/5/2025

marc P.

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Canada

Nous avons pris le forfait 3 nuits-4 jours dans les îles éoliennes, sur le beau voilier de Mario et nous avons adoré l'expérience. Malgré les différences de langue (français, anglais et italien), nous avons très bien su nous comprendre..Mario est patient et fait des efforts pour bien communiquer Mario a su nous accueillir et nous aider a s' installer a bord. Mario nous a fait découvrir les îles et nous a amener dans de superbes criques . On a participer à l'élaboration du trajet , selon nos goûts et nos attentes.. Toujours souriant , Mario nous fait découvrir sa passion et son experience pour la voile ( malheureusement pas beaucoup de vent lors de notre voyage🫤) Mais quand même sorti les voiles quelques fois. Quelle belle expérience ..je recommande a 100%...avec Mario, !!
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Long weekend exploring the Aeolian Islands

06/4/2025

Diane L.

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France

Superbe croisière sur le bateau de Mario ! Nous avons passé un séjour hors du temps entre les îles éoliennes. Il nous apprend aussi bien la voile que l'italien ! Je recommande fortement ce séjour à bord du beau bâteau de Mario.
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Sea, sailing and relaxation in the beautiful Aeolian archipelago

06/4/2025

Deborah R.

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United States

We had a wonderful time! Captain Antonino showed us the beauty and majesty of the Aeolian Islands even better than we could’ve imagined. Our hostess Claudia spoiled us with delicious food at every meal. The trip was truly beyond expectations!

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