
Sailboat yacht sailing holidays & tours in Aeolian Islands
Discover more than 50 opportunities to get on board a Sailboat adventure in Aeolian Islands. A unique experience with a local skipper, starting at €350 a week.
50
experiences

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

4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 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
€525
Per person

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

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

4.9
Italy: Aeolian Islands
7 days - 7 nights
12 departures available
July - November
Starting from
€600
€540
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
6 departures available
July - September
Starting from
€690
€621
Per person

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

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

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

4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
July
€716
Per person

4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
One departure available
September
€700
€665
Per person
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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
1838 reviews
We have known the Aeolian Islands for 20 years, live them with us!
06/29/2026
Gianluca G.
-
IT
A romantic and luxurious vacation in the Aeolian Islands
06/27/2026
Anna D.
-
IT
Four days in the Aeolian Islands from Capo D'Orlando
06/25/2026
Edoardo A.
-
IT
We have known the Aeolian Islands for 20 years, live them with us!
06/24/2026
Alessandro O.
-
IT
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