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

4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

12 departures available

May - October

Starting from

€950

Per person

cover image
avatar image

4.6

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

25 departures available

May - November

Starting from

€1,260

€1,197

Per person

cover image
avatar image

4.8

Super!

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

Italy: Tuscany

7 days - 7 nights

8 departures available

June - September

Starting from

€800

Per person

cover image
avatar image

5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

cover image
avatar image

4.7

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

July - September

Starting from

€1,290

€1,161

Per person

cover image
avatar image

4.8

Super!

From Palermo to Marsala: magical week on a catamaran with hostess

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,450

Per person

cover image
avatar image

4.8

Super!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

3 departures available

August - September

Starting from

€1,100

Per person

cover image
avatar image

4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

23 departures available

May - October

Starting from

€1,320

€1,188

Per person - min 2 pax

cover image
avatar image

4.9

Egadi Islands by catamaran with hostess/cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

June - August

Starting from

€1,100

Per person

cover image
avatar image

4.9

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

Italy: Aeolian Islands

6 days - 7 nights

7 departures available

June - September

Starting from

€945

Per person

cover image
avatar image

4.9

Catamaran between Costa Smeralda, Maddalena and Bonifacio!

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

June - August

Starting from

€1,020

Per person

cover image
avatar image

4.8

Northern Sardinia and Corsica in a large and comfortable Catamaran

Italy: Northern Sardinia

7 days - 7 nights

One departure available

May

€890

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

875 reviews

avatar image

Sailing among the Myths: The Pontine Islands by Catamaran

05/10/2026

DANIELA A.

-

Italy

Alessandro is a topppp!! Take care of everything, I would do it again tomorrow! I didn't know Palmarola, too beautiful from the boat
avatar image

Sailing among the Myths: The Pontine Islands by Catamaran

05/9/2026

Giorgio D.

-

Italy

Beautiful weekend, but much of the credit certainly goes to Alessandro, a skipper capable of transforming a simple experience at sea into something that stays with you. Professional when needed, but above all human, genuine and capable of creating a group without ever forcing anything. He made us all feel at ease from the first moment, with that intelligent lightness that is rare to find today. Always attentive, helpful and with a calm that conveys safety even to those who may not be used to life on a boat. Between laughter, sunsets, chats and simple moments, he managed to create that atmosphere that really makes you disconnect from the routine. Super recommended experience... and skipper who really makes a difference. Thank you Ale, because the sea is beautiful... But the right people make it unforgettable
avatar image

Sailing among the Myths: The Pontine Islands by Catamaran

05/4/2026

Erika P.

-

Italy

I couldn't have had a better group for this experience. I had a catamaran experience that I can call simply extraordinary. From the first moment you could feel an impeccable organization and attention to detail that made everything even more enjoyable. The navigation was relaxing and at the same time exciting, with breathtaking views and stops in crystal clear waters that will remain in my memories for a long time. The catamaran was comfortable, spacious and perfectly equipped, ideal for both relaxing and enjoying the sea in total safety. A special thanks goes to the skipper Alessandro, an extremely professional, competent and always available person. He was able to put everyone at ease, sharing his experience and transmitting great passion for the sea. His ability to handle every situation calmly and confidently and have fun has really made the difference. An experience that I recommend without hesitation to anyone who wants to experience the sea in an authentic and unforgettable way. Congratulations really for the excellent work!
avatar image

The magic of the Egadi Islands aboard a brand new catamaran

10/5/2025

Marco B.

-

Italy

A wonderful experience, sea, great company and fantastic food!

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