experiences

4.8

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - October

Starting from

€950

Per person

5.0

Super!

Week on the Costa Smeralda on a full optional catamaran!

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

July - August

Starting from

€1,150

Per person

4.7

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

8 departures available

August - November

Starting from

€1,455

€1,382

Per person

4.8

Super!

Egadi Islands by catamaran with stewardess and cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

July

Starting from

€1,200

€1,080

Per person

5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

4 departures available

July - August

Starting from

€1,100

€935

Per person

4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

2 departures available

August

Starting from

€1,243

Per person

4.9

Super!

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€870

Per person

4.5

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

€936

Per person

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

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

4.8

Super!

Dream sailing on a fully-equipped catamaran

Italy: Northern Sardinia

7 days - 7 nights

One departure available

July

€990

Per person

4.8

Super!

Dream sailing on a fully-equipped catamaran

Italy: Southern Sardinia

7 days - 7 nights

2 departures available

September

Starting from

€850

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

659 reviews

The magic of the Egadi Islands aboard a brand new catamaran

07/7/2025

fabrizio c.

Italy

Catamarano nuovo, isole e mare bellissimo. Skipper competente e simpatico. Da ripetere!

North Sardinia and South Corsica by catamaran with flybridge

07/1/2025

Mark S.

Germany

Incredible vacation!

Elba and the Tuscan archipelago on board a catamaran

06/30/2025

Stefania B.

Italy

Come prima esperienza di vacanza in barca da sola posso dire che è andata alla grande. Grazie a un tempo favorevole abbiamo raggiunto la Corsica (fantastica) e vissuto tutta la settimana in barca, senza mettere mai piede a terra: quello che volevo. Barca comodissima con spazio per tutti ! Pranzi e cene stellati (in tutti i sensi). Il capitano [hidden] esperto e disponibile, ha condiviso ogni decisione con il gruppo . Cris, suo fidato braccio destro, sempre operativo e paziente a tutte le varie nostre richieste. Esperienza che consiglio vivamente. TORNERÒ SICURAMENTE

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

06/30/2025

Alessandra M.

France

É stata un’esperienza unica, la barca é il modo migliore per visitare le bellissime Eolie. E che barca: un catamarano grande e moderno, con uno skipper esperto ed affidabile affiancato da una bravissima cuoca. L’atmosfera a bordo era perfetta, con il mix ideale di relax e divertimento. Non sono mancate escursioni a terra (trekking su Vulcano e visite ai bellissimi paesi isolani, anche solo per mangiare una granita), nuotate in luoghi segreti meravigliosi, notti in rade silenziose, serate nei locali a terra, aperitivi guardando il tramonto in mezzo al mare… davvero la vacanza perfetta per chi vuole godersi le isole.

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 2035144220

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 (1430)Whole boat with skipper (1115)Cooking service onboard (175)Catamaran (140)Family sailing cruises (130)All inclusive (110)Day trips (110)Courses & regatta (45)WWF Sailing Cruises (40)Sport & wellness (35)

Other travel ideas

Sailboat (499)Whole boat with skipper (389)Cooking service onboard (96)Catamaran (69)All inclusive (57)Family sailing cruises (33)Courses & regatta (27)Day trips (26)Offshore (20)Sport & wellness (17)