
Family sailing cruises yacht sailing holidays & tours in Italy
Discover more than 28 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
28
experiences

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

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

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

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

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

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
3 departures available
July - August
Starting from
€850
€765
Per person

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

4.7
Italy: Liguria
4 days - 4 nights
One departure available
September
€609
€579
Per person

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

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

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
September
€567
Per person

4.9
Super!
Italy: Tuscany
4 days - 4 nights
2 departures available
June
€400
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
385 reviews
June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide
06/10/2026
Guido F.
-
IT
Long weekend of June 2 with WWF guide in the heart of the Tuscan Archipelago
06/10/2026
Enrica Caterina B.
-
IT
2 June: Whale watching expedition with WWF guide on an 18-meter schooner
06/8/2026
Giovanna G.
-
IT
Long weekend of June 2 with WWF guide in the heart of the Tuscan Archipelago
06/4/2026
MARCO C.
-
IT
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