
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.
37
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
881 reviews
Four days among the islands of the Gulf of Naples
06/8/2026
Eleonora S.
-
IT
June 2 long weekend on a catamaran in the Cinque Terre
06/7/2026
LUCA M.
-
IT
The magic of the Egadi Islands aboard a brand new catamaran
06/2/2026
Kris D.
-
BE
The magic of the Egadi Islands aboard a brand new catamaran
06/1/2026
Dalia C.
-
BE
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 20 3514 4220Read our
Contact & SupportItaly: the best travel ideas
Let's talk Sailsquare!



Secure payments



© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964