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.

cover image
avatar image

4.4

Catamaran cruise along the Cilento Coast

Italy: Campania

7 days - 7 nights

4 departures available

June - August

Starting from

€1,150

Per person

cover image
avatar image

New

Day trip to the island of Elba - Porto Azzurro

Italy: Tuscany

1 day - 0 nights

2 departures available

August

€80

Per person

cover image
avatar image

New

Slow sailing in Portoferraio - daily trimaran trip

Italy: Tuscany

1 day - 0 nights

One departure available

August

€80

Per person

cover image
avatar image

New

Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

5 departures available

July - October

Starting from

€238

Per person

cover image
avatar image

3.9

6 days in Costa Smeralda and Northern Sardinia

Italy: Northern Sardinia

5 days - 5 nights

4 departures available

July - August

Starting from

€1,000

Per person

cover image
avatar image
Aeolian Islands by sailboat: 6 days between volcanoes and clear waters

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€6,950

Per person

cover image
avatar image

4.4

Magical Aeolian Islands by catamaran

Italy: Aeolian Islands

7 days - 7 nights

One departure available

July - August

€1,400

Per person

cover image
avatar image

4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - October

Starting from

€1,445

Per person - min 2 pax

cover image
avatar image

New

Weekend a Capraia in Trimarano

Italy: Tuscany

2 days - 1 night

2 departures available

July - August

Starting from

€160

Per person

cover image
avatar image
Sun, sea and relaxation... in the Maddalena archipelago

Italy: Northern Sardinia

6 days - 7 nights

One departure available

July

€1,390

Per person

cover image
avatar image

5.0

Flavors and colors of the Egadi Islands by Catamaran

Italy: Aegadian islands

5 days - 6 nights

One departure available

July

€848

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 - Holidays, Cruises, and Catamaran Trips in Italy

871 reviews

North Sardinia and South Corsica by catamaran with flybridge

07/8/2026

Cristina B.

-

US

The skipper, Antonio, is extremely unprofessional, unwelcoming and incompetent. As we left the dock on our very first sail, he slammed the stern into the dock as he was dropping off a fellow skipper. This was obviously not an experience altering moment, but rather a small foreshadowing of the lack of care this captain would show for his guests and for the boat in general. On the second night of this trip, I was sitting on the forward deck before sunset, when I overheard Antonio, the Captain, sitting atop the flybridge, speaking negatively about me to his girlfriend over the phone. He described to her every communication we had exchanged for two days, Most of which was exaggerated, I assume for the entertainment of his girlfriend, but for me, hearing the Captain belittle me, and lie about me so openly on a public area of the boat during a time in which he should expect his guests are present on the boat was beyond uncomfortable. One of the things he described was the way in which I struggled to swim on a particularly choppy day and complained that he was forced to stand there and watch me swim. I felt so uncomfortable hearing this man complain about me that I called my family in tears. Rather than apologize after he realized I had heard everything he was saying about me, he continued to make snide comments about me to the other guests on board, always assuming I wouldn’t understand because he underestimated my ability to translate. There is no excuse for this level of unprofessionalism. I saved for a year and halted medical treatment to come on this trip because I so badly needed a mental break, to relax and recuperate. Instead, my experience with this captain, was so alienating and distressing, I found myself crying on multiple days in my room, afraid to go on deck or in the other shared areas for fear of more tense interactions or having to overhear his comments about me. Apart from his miserable customer service, I found his piloting of the catamaran to be subpar as well. Every sail felt like slamming and pounding, the boat sounded like it was constantly taking a beating. The back sliding door would be left open to slam against itself over and over as we sailed. I say this to warn the owner of the boat, that if it were my property, I would hire someone who handles it with more delicacy and respect. The bathroom attached to my room was leaking foul smelling water from the floor the entire week. In my attempts to speak to the captain about this or how to better navigate stepping in this foul smelling water each time I entered the bathroom, I was told it was only the sink water and not to worry about it. But really, the smelly water would not have been an issue if I weren’t trapped on a boat with a cartoon super villain for an entire week. I would also reiterate that the other reviews mentioning the fake contracts and relations with Guardia di Finanza are also correct. For anyone reading this, if you are looking to travel alone, especially as a woman, I would not sail with this skipper. I didn’t feel safe or comfortable and these trips are entirely too expensive to risk having some miserable man talk down to you and treat you like you’re second class. Pick another captain.
avatar image

Weekend along Ponza and Palmarola by catamaran

07/7/2026

Samuel L.

-

SM

Crazy weekend, We found great guys to share the boat with us. Angelo the skipper always super helpful and then with his secret on the boat he still makes everything crazy 🔥 Super recommended can't wait to go back

Magical Aeolian Islands on a catamaran with a hostess on board

07/5/2026

Giulia M.

-

IT

Beautiful holiday suitable for those who love boat life. The skipper Alessandro and the hostess Helena made the holiday pleasant and were always ready to meet the guests' requests. See you at the next destination!
avatar image

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

07/5/2026

Francesca B.

-

IT

Simply memorable sailing holiday. The sea does its part, the sparses as well, the aperitifs at sunset too. But the real difference is made by the skipper. [hidden] leaves nothing to chance: he already thinks about the next step, assesses the conditions and always makes you feel safe. He took us every time where it made the most sense to go to make us experience the best possible "holiday simulation": beautiful roadsteads, right rhythms, choices made with criteria and attention even to those details that really matter, such as sleeping well and "dancing" as little as possible at anchor. Behind every decision it was clear that there was always a plan A, B and C: everything designed to make us feel good, enjoy the sea and feel in the right place at the right time. The explanations during navigation are also beautiful: clear, interesting. They make you better understand where you are, what you are experiencing and why you are enjoying it even more. Special mention also for Manu, always available and super pleasant on board. It really was the perfect vacation simulation! Top emulsified experience. I got off the boat with a huge desire to start again. With [hidden] you are on the safe side. Literally.

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