
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.
11
experiences

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

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

4.1
Italy: Aeolian Islands
6 days - 7 nights
2 departures available
September - October
Starting from
€680
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€700
€630
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
September - October
€980
Per person

5.0
Italy: Aeolian Islands
6 days - 7 nights
4 departures available
September - October
Starting from
€607
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
€730
Per person

5.0
Italy: Aeolian Islands
2 days - 2 nights
3 departures available
September
€723
Per person

4.9
Italy: Aeolian Islands
6 days - 7 nights
One departure available
September
€945
Per person

5.0
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September
€800
Per person

4.7
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September
Starting from
€690
Per person - min 2 pax
Why book a holiday with Sailsquare?
The world's largest marketplace for sailing holidays
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 - Private yacht sailing holidays with skipper in the Aeolian Islands
669 reviews
Unforgettable adventure in the Aeolian Islands
09/7/2026
Elisabetta M.
Aeolian Islands on a luxury sailing boat
09/6/2026
isabella d.
-
IT
Aeolian Islands on a luxury sailing boat
09/6/2026
Palma A.
-
IT
A week in the Aeolian Islands - 6 islands in seven days
09/6/2026
Giorgia Z.
-
IT
Customer Support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 20 3514 4220Read our
Contact & SupportCan't find the perfect holiday for you?
Tell us what you are looking for and let our team find the right solution for you!
Let's talk Sailsquare!



Secure payments



© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964