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Sailboat yacht sailing holidays & tours in Aeolian Islands

Discover more than 49 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!

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

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

June - October

Starting from

€689

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

June - October

Starting from

€650

Per person

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4.8

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

7 departures available

June - September

Starting from

€583

€525

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

20 departures available

May - November

Starting from

€600

€540

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€750

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

11 departures available

May - October

Starting from

€800

€720

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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4.8

Super!

Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

May - September

Starting from

€700

€630

Per person

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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

June

€400

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

21 departures available

May - November

Starting from

€420

€399

Per person

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4.9

Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic

Italy: Aeolian Islands

5 days - 5 nights

7 departures available

June - August

Starting from

€590

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

4 departures available

June - September

Starting from

€400

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Aeolian Islands

1821 reviews

Let's discover the Aeolian Islands together by sailing

05/17/2026

Tim D.

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Germany

Mario is an excellent skipper. Through him we were able to see the most beautiful corners of the Aeolian Islands. His local knowledge and contacts on all the islands gave us an unforgettable trip. We were also lucky enough to have his incredibly lovely wife on board. Even though communication was not easy (we didn't speak Italian and she didn't speak English), she made the trip even more beautiful. We thank them very much for this wonderful sailing holiday.

End of season weekend in the Aeolian Islands

11/3/2025

Collwyn Y.

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Italy

I come from the North Sea but I now live the Italian Alps and I’ve been really missing the ocean. So, after much thinking, I decided to treat myself to a little sailing holiday in October. [hidden] (the boat) is cozy yet has every comfort and the hosts really make you feel like you’re being treated to an Italian family gateway. Giacomo and Laura go above and beyond to fit everyone's need and requests. They exceeded my expectations! Great company, great food and insane landscapes! Nothing quite like sleeping under the stars, lulled by the gentle rocking of the boat. Thank you, I hope next time I can bring my family from Scotland!
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End of season weekend in the Aeolian Islands

11/3/2025

Gaia R.

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Italy

Honestly, I had underestimated a sailing holiday in Sicily in October but instead it was unforgettable. The Aeolian Islands are even more beautiful in this period, being less crowded. Living them from the sea, guided by two local people, then, becomes a truly authentic experience! Thank you Giacomo and Thank you Laura, we will definitely be back this summer to be able to have even more fun with the longer 🌬️ days

End of season weekend in the Aeolian Islands

11/3/2025

Edoardo T.

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Italy

End of October, I still want summer and I decide to do a little madness... on a sailing boat to the Aeolian Islands!! I was undecided but in the end I threw myself into it and I couldn't have made a better choice. The best boat, the best crew: the company, the food... everything really great!! What can I say: I'll be back in the summer!!

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