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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.

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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

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4.7

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

39 departures available

April - November

Starting from

€1,640

€1,558

Per person - min 2 pax

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5.0

Super!

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

One departure available

September

€212

Per person

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4.8

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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4.8

Super!

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

Italy: Tuscany

7 days - 7 nights

2 departures available

September

€850

Per person

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4.5

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

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4.6

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

One departure available

September

€620

€558

Per person

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4.9

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

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

€980

Per person

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Day Cruise - Gulf of Poets Tour

Italy: Liguria

1 day - 0 nights

18 departures available

September - October

Starting from

€71

Per person

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4.3

Catamaran cruise along the Cilento Coast

Italy: Campania

7 days - 7 nights

One departure available

June - July

€1,150

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€945

Per person

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4.7

Cruise to Naples and Amalfi Coast

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

September

€590

Per person

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Reviews - Holidays, Cruises, and Catamaran Trips in Italy

1019 reviews

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Summer 2026 - Catamaran week in the Pontine Islands

09/6/2026

Maurizio M.

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IT

Cccvvbbbn

Sail to the Aeolian Islands with an experienced crew on a catamaran!

09/6/2026

Lorenzo A.

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IT

Strongly negative experience and holiday compromised by questionable management to say the least. Our experience was ruined mainly by the management of skipper Andrea and, more generally, by a series of inefficiencies that we consider unacceptable. On the day of boarding, scheduled at 18:00, at 17:55 we were still on the platform without Andrea having shown up. Only a few minutes after boarding we received a phone call in which we were informed that, together with another couple, we had been transferred to a sailboat with another skipper. It was, in fact, a downgrade compared to the catamaran that had been assigned to us, on which we were supposed to live the experience with skipper and co-skipper. The reason we were given was that of "overbooking". A paradoxical situation, considering that Andrea would have directly accepted further personal bookings, thus coming to no longer have room for people who had been regularly assigned to his crew through Sailsquare. The thing that we consider even more serious is that there are conversations, WhatsApp messages, communications via e-mail and via Sailsquare in which Andrea expressly confirms our presence on board, mine and my girlfriend's. It was therefore not an improvised last-minute assignment: our presence on the catamaran had been agreed and confirmed. Our story had already begun with a change of skipper. Initially we were assigned to Emanuele, Andrea's son, who canceled the tour about six days before departure due to problems with the boat. A situation that can certainly happen and that, taken individually, we would have understood. The problem is that we had already organized and paid for four flights and a three-day stay in Stromboli, just for the Sailsquare tour. We had therefore already incurred important expenses and organized our entire holiday, trusting in the alternative that had been proposed to us. To meet the discomfort, Sailsquare had assigned us to Andrea with a catamaran upgrade, together with another couple. The assignment had been regularly accepted and confirmed by Andrea himself through the various communication channels. For this reason, in our opinion, talking about "overbooking" later is not an acceptable justification. In the end we were transferred to a third boat, a sailboat that was filled on the day of embarkation until we reached about 10 people. On board we also met another guy who, like us, had initially been assigned to Emanuele and who confirmed to us that he had experienced the same situation. What made the experience even more unpleasant was the subsequent behavior. The new skipper, Matteo, has repeatedly expressed his problem with the non-payment of fees for the additional people he had embarked. We were asked to urge Sailsquare to resolve the economic situation as soon as possible, despite the fact that we had regularly paid Sailsquare for our trip. The situation has reached the point that we have also been offered the possibility of having to disembark in the middle of the week if the payment was not resolved. Although this eventuality fortunately did not occur, we consider it absurd that a customer who has regularly paid should spend his holiday with the doubt of being able to be disembarked due to administrative problems between the platform, skipper and boat. Andrea's behavior, which we perceived as arrogant, insolent and totally unprofessional, was for us the most serious point of the story. We do not dispute the fact that unforeseen events or changes of plans may occur: we dispute the way they were handled, just a few minutes before boarding and without any real choice. Behind a holiday of this type there are months of work, money, organization and expectations. You work all year round to be able to go on vacation, and being on the quay five minutes before boarding without knowing what would happen is a situation that should never be experienced by a customer. We believe that there have been serious shortcomings of organization, communication and professionalism, both in the management by Sailsquare and in the behavior of the skipper Andrea. A holiday can be changed due to an unforeseen event. What should never change is respect for customers.

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/6/2026

Natalia C.

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IT

Extraordinary week between crystal clear sea, relaxation and excellent food. The boat is cozy and perfect for life on board, but the real added value was the skipper Umberto. Sunny, overwhelming and with a contagious irony. He was able to create a super close-knit atmosphere between all of us from day one, making us immediately feel like a group of old friends. In addition to guaranteeing perfect navigation and in total safety, it was the soul of the holiday between laughter, aperitifs at sunset and unforgettable moments. We will definitely be back on board with him. Fundamental, and the perfect shoulder for Umberto was Monica. Not just a hostess. He is almost an engineer with a passion for the sea and good food. His kindness, his education and his never making a mistake in a dish or a word, were the perfect side dish. Highly recommended all: Monica, Umberto and the catamaran ♥️ I forgot Gigia: adorable!

Sail to the Aeolian Islands with an experienced crew on a catamaran!

09/5/2026

serena s.

-

IT

One of the most beautiful charter cruises ever done! Enchanting Aeolian Islands. Catamaran [hidden] very welcoming, fantastic skippers and great food on board. Nothing was missing. I would leave with them tomorrow ... Highly recommended

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