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

4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

June - October

Starting from

€650

Per person

4.8

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€500

Per person

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

June - November

Starting from

€600

€540

Per person

4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

July - November

Starting from

€540

€513

Per person

4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

June

€400

€370

Per person

4.9

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€945

Per person

4.9

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

Italy: Aeolian Islands

5 days - 5 nights

4 departures available

June - August

Starting from

€590

Per person

4.9

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

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

July - September

Starting from

€750

Per person

4.8

Super!

Relax alle Eolie con stile - Hostess Inclusa!

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - December

Starting from

€525

Per person

4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€1,000

Per person

4.8

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

5.0

Aeolian Islands made to measure – Exclusive Offshore Sailing

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

June - July

Starting from

€1,200

Per person

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Reviews - Private yacht sailing holidays with skipper in the Aeolian Islands

475 reviews

Let's discover the Aeolian Islands together by sailing

05/17/2026

Tim D.

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.

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.

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.

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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