
Yacht sailing holidays & skippered tours in Italy
Discover more than 9 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
9
experiences

4.6
Premium
Italy: Northern Sardinia
7 days - 7 nights
One departure available
October - November
Starting from
€1,125
Per person - min 2 pax
4.6
Italy: Tuscany
2 days - 2 nights
5 departures available
October - November
Starting from
€300
€270
Per person

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

New
Italy: Tuscany
2 days - 2 nights
One departure available
October - November
€250
Per person

5.0
Italy: Liguria
2 days - 2 nights
One departure available
October - November
Starting from
€380
Per person

4.8
Italy: Pontine Islands
3 days - 2 nights
One departure available
November
Starting from
€225
Per person

4.5
Italy: Aegadian islands
7 days - 7 nights
One departure available
October - November
Starting from
€580
Per person

4.8
Italy: Pontine Islands
4 days - 3 nights
One departure available
November
Starting from
€225
Per person

4.8
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€430
Per person
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 - Yacht sailing holidays & skippered tours in Italy
13883 reviews
Summer is made for the Aeolian Islands! Weekly cruise
06/11/2026
Patrizia R.
-
IT
June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide
06/10/2026
Guido F.
-
IT
Weekend in Ischia and Ventotene: History and Nature
06/10/2026
Michele F.
-
IT
June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene
06/10/2026
Donatella L.
-
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 & SupportLet's talk Sailsquare!



Secure payments



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