
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.
49
experiences

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
13 departures available
June - October
Starting from
€689
Per person

4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
7 departures available
June - October
Starting from
€650
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
7 departures available
June - September
Starting from
€583
€525
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
20 departures available
May - November
Starting from
€600
€540
Per person
4.9
Italy: Aeolian Islands
6 days - 7 nights
6 departures available
June - September
Starting from
€750
Per person

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
11 departures available
May - October
Starting from
€800
€720
Per person

5.0
Super!
Italy: Aeolian Islands
3 days - 2 nights
10 departures available
June - August
Starting from
€390
€351
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
3 departures available
May - September
Starting from
€700
€630
Per person

4.9
Super!
Italy: Aeolian Islands
3 days - 3 nights
One departure available
June
€400
Per person

4.5
Italy: Aeolian Islands
7 days - 7 nights
21 departures available
May - November
Starting from
€420
€399
Per person

4.9
Italy: Aeolian Islands
5 days - 5 nights
7 departures available
June - August
Starting from
€590
Per person

4.9
Super!
Italy: Aeolian Islands
4 days - 4 nights
4 departures available
June - September
Starting from
€400
Per person
Why book a holiday with Sailsquare?
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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
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 more about the skipper and travellers who have already booked the holiday, to find out more about the
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
1821 reviews
Let's discover the Aeolian Islands together by sailing
05/17/2026
Tim D.
-
Germany
End of season weekend in the Aeolian Islands
11/3/2025
Collwyn Y.
-
Italy
End of season weekend in the Aeolian Islands
11/3/2025
Gaia R.
-
Italy
End of season weekend in the Aeolian Islands
11/3/2025
Edoardo T.
-
Italy
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