header cover
logo

Log in

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.

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

1068 reviews

avatar image

Aeolian Islands in a big and new catamaran: sea, sun, relaxation

10/4/2026

Loredana T.

-

IT

A simply wonderful week, made even more special by the skipper who accompanied us and his beautiful catamaran. Maurizio is a very kind, respectful person, he is very helpful. He was able to create a beautiful balance between professionalism and conviviality, making us always feel at ease and allowing us to experience the sea with lightness and serenity. I couldn't have had a better skipper. Thank you for this wonderful week ❤️⛵️
avatar image

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

10/1/2026

Federica P.

A fantastic week!!
avatar image

Weekend catamaran in Portovenere and Cinque Terre

09/29/2026

Coretta P.

-

IT

Antonio proved to be a very knowledgeable, organized, helpful and patient owner/skipper. The catamaran was found to be particularly comfortable and well maintained. Splendid itinerary and the weather also favored us. In short, a beautiful weekend!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

09/29/2026

Sergio V.

-

IT

Alessandro is first of all a great person, then as far as the week is concerned he proved to be available and attentive to the requests and desires of the crew, precious for suggestions and advice on what to do. He always accompanied us even on the ground. Helena, passionate about her work, has always prepared different dishes that are satisfying for the taste and for the eyes. It couldn't have been better than this!

Customer Support

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!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Italy: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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