
Holidays, Cruises, and Catamaran Trips in Italy
The unique experience of sailing on a catamaran, with its spacious layout and exceptional comfort, combined with the chance to explore Italian coasts accessible only by sea and share moments with new friends, makes every holiday unforgettable. Treat yourself to a vacation where you wake up in a bay and enjoy breakfast surrounded by the beauty of the sea.
14
experiences
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 - Holidays, Cruises, and Catamaran Trips in Italy
818 reviews
The magic of the Egadi Islands aboard a brand new catamaran
10/5/2025
Marco B.
-
Italy
Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42
09/29/2025
Stella H.
-
France
Weekend in catamarano a Portovenere e Cinque Terre
09/29/2025
Valentina D.
-
Italy
Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42
09/28/2025
Sara D.
-
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