header cover
sailsquare logo

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

4.8

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

4 departures available

August - October

Starting from

€950

Per person

cover image
avatar image

4.6

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

July - September

Starting from

€1,040

€988

Per person

cover image
avatar image

4.8

Super!

Egadi Islands by catamaran with stewardess and cook on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

July

€1,350

€1,215

Per person

cover image
avatar image

4.7

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

9 departures available

August - November

Starting from

€1,455

€1,382

Per person

cover image
avatar image

5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€1,300

Per person

cover image
avatar image

4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

One departure available

August

€1,573

Per person

cover image
avatar image

4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

July - October

Starting from

€1,800

Per person

cover image
avatar image

4.8

Super!

Dream sailing on a fully-equipped catamaran

Italy: Southern Sardinia

7 days - 7 nights

3 departures available

August - September

Starting from

€850

Per person

cover image
avatar image

4.6

3 days in Sardinia - Costa Smeralda or AMP Tavolara

Italy: Northern Sardinia

3 days - 3 nights

2 departures available

July - September

Starting from

€660

Per person

cover image
avatar image

4.8

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

August - September

€1,300

Per person

cover image
avatar image
Discovering the Aeolian Islands by catamaran with hostess

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August - September

€1,250

Per person

cover image
avatar image
Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

4 departures available

September

Starting from

€650

€585

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

668 reviews

avatar image

The magic of the Egadi Islands aboard a brand new catamaran

07/16/2025

Roberta M.

-

Italy

Thanks to Timoti, aka Captain (skipper), and Giuseppe's team for this fantastic experience. What can I say, the Egadi islands are wonderful and certainly do not need my praise. It was my first holiday at sea, and I doubt it will be my last! The catamaran was comfortable and well designed: with six people (including the skipper), you never feel cramped. Everything is functional and in very good condition — it really feels like new, or at least maintained with great care. If we want to be really picky, perhaps we could find a better way to create a little more storage/space in the sleeping cabins (for example, a shelf near the side/head of the bed of those who do not have access to the bedside table), always accepting the limitations of the structure. And for those who are new to this type of experience, it might be useful to receive the famous shopping options list in advance, so you already arrive with some ideas on the first day. It is absolutely not meant to be a criticism, but a constructive suggestion to make an already fantastic experience... even better! Special thanks to Timoti: in addition to being very nice, present, full of ideas and suggestions but always discreet and helpful, he also improvised himself as a chef, cooking real delights – from tuna tartare to an amatriciana with a bacon that cannot be explained!
avatar image

Dream sailing on a fully-equipped catamaran

07/16/2025

Alessia P.

-

Italy

THE MOST RELAXING HOLIDAY I'VE EVER HAD. Comfortable boat equipped with everything, large and well-kept spaces! The highlight of the experience is definitely the crew: The captain very experienced and very nice, shared every decision with the group and cheered us up with his stories from all over the world; Cris, his trusted right-hand man, always operational and patient ready to meet the requests of the whole group. AUTHENTIC EXPERIENCE. I RECOMMEND IT WITHOUT ANY DOUBT
avatar image

North Sardinia and South Corsica by catamaran with flybridge

07/14/2025

francesca f.

-

Italy

The boat was very nice, comfortable and spacious. The environment is clean. The kitchen is large and comfortable. The only drawback: this type of boat does not offer great fun while sailing because it is not always possible to hoist the sails... Comfort is preferred to sailing. Antonio was a very good skipper, careful to meet the multiple needs of the whole crew. He made us discover wonderful places that will remain in our hearts.
avatar image

Magical Aeolian Islands by catamaran

07/14/2025

Ciro C.

-

Italy

Amazing skipper,, cook and boat

Customer Support

nightLifeGeneralInfo

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!

search

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