
Sailboat yacht sailing holidays & tours in Aeolian Islands
Discover more than 44 opportunities to get on board a Sailboat adventure in Aeolian Islands. A unique experience with a local skipper, starting at €350 a week.
44
experiences

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
August - October
Starting from
€690
Per person

4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
July - October
Starting from
€700
Per person

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

4.5
Italy: Aeolian Islands
7 days - 7 nights
12 departures available
August - November
Starting from
€540
€513
Per person

4.8
Super!
Italy: Aeolian Islands
5 days - 6 nights
One departure available
July
€590
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€900
€750
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€750
€675
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
9 departures available
July - October
Starting from
€750
€675
Per person

5.0
Italy: Aeolian Islands
6 days - 7 nights
One departure available
August
€1,050
Per person

5.0
Italy: Aeolian Islands
3 days - 2 nights
6 departures available
July - August
Starting from
€390
€351
Per person

5.0
Super!
Italy: Aeolian Islands
6 days - 7 nights
3 departures available
August - September
Starting from
€950
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
July - September
Starting from
€850
€650
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.
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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 - Sailboat yacht sailing holidays & tours in Aeolian Islands
1842 reviews
Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic
07/6/2026
Vitaliano T.
-
IT
An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands
07/5/2026
Monica Sofia S.
-
IT
Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic
06/30/2026
Iole D.
-
BE
Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic
06/30/2026
Simona O.
-
IT
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