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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.

experiences

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

Per person

5.0

Super!

In the Aeolian Islands with chef on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July

€1,000

Per person

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

4.6

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

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - August

Starting from

€910

€865

Per person - min 2 pax

5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Italy: Aeolian Islands

4 days - 4 nights

14 departures available

April - October

Starting from

€400

Per person

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

€650

Per person

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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

475 reviews

End of season weekend in the Aeolian Islands

11/3/2025

Collwyn Y.

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!

End of season weekend in the Aeolian Islands

11/3/2025

Gaia R.

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.

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!!

End of season weekend in the Aeolian Islands

11/3/2025

Francesco P.

Italy

I have always dreamed of taking a sailing holiday and I treated myself to a mini-weekend in October: reality exceeded expectations! The Aeolian Islands are fantastic islands, the colors of the landscape surreal. Sturdust and his crew an excellent company. Thanks to Giacomo and Laura for their hospitality, 5 well-deserved stars on everything!

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