
Family sailing cruises yacht sailing holidays & tours in Italy
Discover more than 23 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
23
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
7 departures available
July - September
Starting from
€700
Per person

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

4.7
Italy: Tuscany
6 days - 6 nights
2 departures available
August - September
Starting from
€1,041
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€1,100
Per person

4.7
Italy: Tuscany
6 days - 7 nights
2 departures available
July - August
Starting from
€1,052
Per person

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

4.8
Super!
Italy: Tuscany
5 days - 4 nights
4 departures available
July - September
Starting from
€490
€466
Per person

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

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

4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
€441
Per person

4.7
Italy: Liguria
6 days - 6 nights
2 departures available
July - August
Starting from
€946
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
2 departures available
July
Starting from
€590
€531
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
394 reviews
All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company
07/6/2026
Matteo D.
-
IT
All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company
07/4/2026
Erica M.
-
IT
All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company
07/4/2026
Maurizio N.
-
IT
Mini-cruise with WWF guide in the heart of the Tuscan Archipelago
07/2/2026
Bianca Matelda C.
-
IT
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