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Sailboat yacht sailing holidays & tours in Aeolian Islands

Discover more than 48 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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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - October

Starting from

€751

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

2 departures available

July - August

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

8 departures available

September - November

Starting from

€530

€477

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

6 departures available

August - 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

11 departures available

July - October

Starting from

€530

€504

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

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

Italy: Aeolian Islands

5 days - 4 nights

7 departures available

August - October

€590

Per person

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4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€640

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

3 departures available

July - August

Starting from

€910

€819

Per person - min 2 pax

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4.9

Aeolian Islands on a luxury sailing boat

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

July - August

Starting from

€700

€500

Per person

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4.8

Super!

Discovering the Aeolian islands: nature, relaxation and fun

Italy: Aeolian Islands

7 days - 7 nights

3 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

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

1591 reviews

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

07/8/2025

Marco C.

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Italy

Ci sono viaggi che restano nella pelle come il sale dopo una lunga nuotata. La nostra esperienza alle Eolie, 8 amici in barca a vela con Antonio è stata proprio questo: un’immersione nella bellezza, nella quiete e nell’autenticità. La barca, tenuta con cura e amore, era il nostro rifugio galleggiante, da cui ogni giorno partivano nuove esplorazioni. Le spiagge e i litorali che Antonio ha saputo farci scoprire erano angoli nascosti e mai banali, dove il tempo sembrava dilatarsi. Le lunghe nuotate esplorative tra calette selvagge, fondali trasparenti e scogli scolpiti dal vento rimarranno tra i ricordi più vivi e intensi. Anche a terra, ogni tappa era un piccolo incanto: ristoranti selezionati con gusto, locali autentici e pieni di atmosfera, sapori semplici e veri come il mare che ci cullava. Antonio non è stato solo il nostro skipper, ma un compagno di viaggio capace di farsi parte del gruppo con naturalezza. Con la sua calma, la sua simpatia e quella serenità che sembra venire direttamente dal mare, ha reso questa esperienza unica, vera, piena di armonia. Una vacanza che ha il sapore del vento, della libertà e delle cose belle che non si dimenticano. Grazie Antonio, ci hai regalato una vacanza che porteremo nel cuore.
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We circumnavigate the Aeolian Islands starting from Vulcano

07/8/2025

Federica R.

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Italy

Con Alice e [hidden] si vive la vera esperienza di vacanza in barca! Posti molto belli di relax pace e natura!
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Aeolian Islands: between sea and authentic flavours

07/7/2025

Achille V.

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Italy

Abbiamo vissuto un' esperienza indimenticabile in luoghi incantevoli. Anche grazie alla competenza e simpatia di Emiliano e Nila.
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/7/2025

Elisa S.

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Spain

Dario è stato un capitano eccezionale! Attento, disponibile, saggio e prudente. Organizzazione e itinerario perfetti. Consigli da vero local impagabili. La barca è tenuta come un gioiellino. Comoda, pulita ordinata e bien organizzata. Grazie a Dario e al resto della ciurma per questa bellissima vacanza

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