
Family sailing cruises yacht sailing holidays & tours in Italy
Discover more than 22 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
22
experiences

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

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

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

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
5 departures available
June - August
Starting from
€800
€720
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
One departure available
April
€275
Per person

4.7
Italy: Pontine Islands
5 days - 4 nights
One departure available
May - June
€567
Per person

4.7
Italy: Liguria
3 days - 3 nights
One departure available
April
€452
Per person

4.8
Italy: Tuscany
4 days - 3 nights
10 departures available
April - September
Starting from
€310
€279
Per person

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

4.7
Italy: Liguria
3 days - 3 nights
One departure available
April
€452
€429
Per person

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

4.7
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
July - September
Starting from
€999
€949
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
371 reviews
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
Poetic Gulf of Poets
10/6/2025
Fabiola R.
-
Italy
Poetic Gulf of Poets
10/6/2025
Domenico C.
-
Italy
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