
Family sailing cruises yacht sailing holidays & tours in Italy
Discover more than 25 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
25
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - September
Starting from
€680
Per person

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

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
12 departures available
June - September
Starting from
€550
€523
Per person

4.7
Italy: Tuscany
6 days - 6 nights
4 departures available
August - September
Starting from
€1,041
€989
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
12 departures available
May - September
Starting from
€400
Per person

4.7
Italy: Tuscany
6 days - 7 nights
5 departures available
July - August
Starting from
€1,094
€1,039
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
August
Starting from
€1,100
€990
Per person

4.9
Super!
Italy: Tuscany
4 days - 4 nights
3 departures available
June
€400
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
7 departures available
June - July
Starting from
€490
Per person

4.8
Italy: Tuscany
4 days - 3 nights
7 departures available
July - September
Starting from
€400
€360
Per person

4.7
Italy: Liguria
4 days - 4 nights
3 departures available
June - September
€609
€579
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
373 reviews
Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide
04/8/2026
Agnese F.
-
Italy
Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide
04/7/2026
Sara B.
-
Italy
We have known the Aeolian Islands for 20 years. - Live them with us.
10/20/2025
Marco F.
-
Italy
Poetic Gulf of Poets
10/9/2025
Massimo G.
-
Italy
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