Family sailing cruises yacht sailing holidays & tours in Italy
Discover more than 26 opportunities to get on board a Family sailing cruises adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
26
experiences
26
experiences
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
5 departures available
July - September
Starting from
€650
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
August - October
Starting from
€200
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
July - August
Starting from
€935
€748
Per person
4.7
Italy: Tuscany
6 days - 6 nights
4 departures available
July - September
Starting from
€1,041
€989
Per person
5.0
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August - November
Starting from
€650
€585
Per person
4.7
Italy: Liguria
5 days - 6 nights
4 departures available
July - September
Starting from
€830
€789
Per person
4.7
Italy: Tuscany
6 days - 7 nights
7 departures available
July - September
Starting from
€1,041
€989
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
5 departures available
September - October
Starting from
€294
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
7 departures available
July - September
Starting from
€550
€523
Per person
4.6
Italy: Tuscany
7 days - 6 nights
6 departures available
July - September
Starting from
€600
Per person
4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€420
€399
Per person
4.7
Italy: Liguria
6 days - 6 nights
2 departures available
July - August
Starting from
€925
€879
Per person
Why book a holiday with Sailsquare?
The world's largest marketplace for sailing holidays
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
171 reviews
Whale watching cruise with WWF guide between Elba, Pianosa and the canyons of Corsica
07/2/2025
Veronica S.
-
Italy
Aeolian Islands - A week on a sailing boat with skipper and assistant
07/1/2025
Rodolfo B.
-
Italy
Whale watching cruise with WWF guide between Elba, Pianosa and the canyons of Corsica
06/30/2025
Carla M.
-
Italy
Aeolian Islands - A week on a sailing boat with skipper and assistant
06/29/2025
Andrea M.
-
Italy
Customer Support
Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 2035144220Read our
Contact & SupportItaly: the best travel ideas
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964