experiences

4.7

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

37 departures available

April - November

Starting from

€1,640

€1,558

Per person - min 2 pax

4.9

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

€980

Per person

4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

26 departures available

May - October

Starting from

€1,320

€1,056

Per person - min 2 pax

Day Cruise - Gulf of Poets Tour

Italy: Liguria

1 day - 0 nights

4 departures available

September - October

Starting from

€71

Per person

4.3

Catamaran cruise along the Cilento Coast

Italy: Campania

7 days - 7 nights

One departure available

June - July

€1,150

Per person

New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

31 departures available

September - October

Starting from

€150

Per person

Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

One departure available

October

€238

Per person

4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

25 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

2 departures available

September - October

Starting from

€950

Per person

New

Gulf of Poets: Shared Sunset Tour by Catamaran

Italy: Liguria

1 day - 0 nights

33 departures available

September - October

Starting from

€120

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

1056 reviews

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

09/23/2026

Kim W.

Just an amazing week: great boat (the Bali 5.8), wonderful crew, and amazing destinations, A minor improvement could have been the pre-trip communication from the My Sailing office, while very responsive to initial queries, comms could have been more proactive as time of the trip was getting nearer.

Weekend catamaran in Portovenere and Cinque Terre

09/22/2026

Alessandra G.

Welcoming, kind and fun lo.skipper, amused and treated with kindness

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/22/2026

Paolo C.

The wonderful places visited certainly do not need approval but certainly the added value of this experience were Fabrizio and Monica. Two people who were always smiling and helpful who allowed us to live a week difficult to forget but above all thanks to them we really 'disconnected' from a long and difficult work routine. Fabrizio, our captain, a welcoming guy and always available. Monica welcomed us every morning with a smile and a thousand delicious dishes. Really two people out of the routine and therefore absolutely exceptional. Thank you very much

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/22/2026

Marcella L.

I spent a wonderful week on board the catamaran discovering the Aeolian Islands together with a group of great people! It was the perfect choice to experience this archipelago to the fullest. Every day a different emotion and spectacular bays in which to wake up. A special thanks to Fabrizio, who with great professionalism and sympathy guided us to the best moorings, always anticipating the weather and to Monica the Super Hostess who pampered us throughout the week with her desserts and excellent cuisine. 100% recommended holiday

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 4220

Read our

Contact & Support

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

Sailboat (380)Whole boat with skipper (280)Cooking service onboard (80)Catamaran (50)All inclusive (40)Day trips (35)Courses & regatta (30)Sport & wellness (25)Family sailing cruises (10)Offshore (5)

Other travel ideas

Sailboat (124)Whole boat with skipper (106)Cooking service onboard (58)Catamaran (43)All inclusive (33)Exotic destinations (25)Courses & regatta (14)Offshore (11)Day trips (7)Sport & wellness (6)