
Family sailing cruises yacht sailing holidays & tours in Italy
Discover more than 18 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
18
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August
Starting from
€920
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
3 departures available
August - September
Starting from
€600
€570
Per person

4.7
Italy: Tuscany
6 days - 6 nights
One departure available
August - September
€1,041
Per person

4.8
Super!
Italy: Tuscany
4 days - 3 nights
4 departures available
August - September
Starting from
€400
€360
Per person

4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€452
€429
Per person

4.7
Italy: Tuscany
7 days - 6 nights
6 departures available
August - September
Starting from
€700
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€690
€613
Per person

4.7
Italy: Liguria
6 days - 6 nights
One departure available
July - August
€946
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
7 departures available
August - October
Starting from
€750
€675
Per person

4.7
Italy: Liguria
4 days - 4 nights
2 departures available
September
€609
€579
Per person

4.9
Super!
Italy: Tuscany
4 days - 4 nights
2 departures available
September
€400
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
3 departures available
September
€490
€466
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 - Family sailing cruises yacht sailing holidays & tours in Italy
418 reviews
Sailing cruise to the Pontine: wonders a stone's throw from Rome
07/22/2026
Francesca C.
-
IT
Sailing cruise to the Pontine: wonders a stone's throw from Rome
07/22/2026
marco s.
-
IT
Sailing cruise to the Pontine: wonders a stone's throw from Rome
07/22/2026
Luigi F.
-
IT
Cruise with WWF guide between Giglio, Giannutri and Montecristo
07/21/2026
Fabio U.
-
IT
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