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
18
experiences
4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
€419
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€750
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
4 departures available
September - October
Starting from
€220
Per person
4.8
Super!
Italy: Tuscany
4 days - 3 nights
One departure available
September
€360
€342
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
September
€350
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
5 departures available
September - October
Starting from
€363
€290
Per person
4.7
Italy: Tuscany
7 days - 6 nights
3 departures available
September
Starting from
€600
Per person
4.7
Italy: Tuscany
6 days - 6 nights
One departure available
August - September
€1,041
€989
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
2 departures available
August - September
Starting from
€550
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - November
€583
Per person
4.7
Italy: Naples & Amalfi Coast
3 days - 3 nights
2 departures available
September
Starting from
€452
€429
Per person
4.6
Italy: Tuscany
7 days - 7 nights
One departure available
August
€896
€806
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
298 reviews
Aeolian Islands - A week on a sailing boat with skipper and assistant
08/20/2025
Rosamaria S.
-
Italy
Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms
08/20/2025
Giulia D.
-
Italy
Weekend on a sailing boat between Capraia and Elba
08/19/2025
Carlotta Giulia S.
-
Italy
Weekend on a sailing boat between Capraia and Elba
08/19/2025
Michela D.
-
Italy
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