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Yacht sailing holidays & skippered tours in Italy

Discover more than 9 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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The world's largest marketplace for sailing holidays

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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 - Yacht sailing holidays & skippered tours in Italy

13167 reviews

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Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin

08/22/2025

Silvia R.

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Italy

Thank you for this holiday! Both for the experience and the group, and for the couple Andrea and Sara, who led us around the archipelago and the south of Corsica. They know very well the places we visited and we were able to see almost deserted bays even the week of Ferragosto! Thank you and see you next time!
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Lampedusa, Linosa and Lampione, islands on the high seas

08/22/2025

Manuela B.

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Italy

It was supposed to be two skippers and in the end there was only Lorenzo who in that week definitely lacked empathy. Excellent cook and I would say good skipper (we had good weather conditions anyway, so I can't say much more). If you want a quiet holiday without music, without revelry and you are a good swimmer (Lorenzo anchors the boat and clearly tells you that to reach the beaches you have to swim...... and who is not a good swimmer... patience..). I recommend it. If you want, as I have always had, a skipper who makes himself available to the crew, despite the little propensity, in various situations (tender, music, and more) look for something different. However, thanks to all the guys I met this week who made this holiday beautiful. Lampedusa and Linosa are two masterpieces of nature!
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Different Flotilla: Party and new friends in the Aeolian Islands

08/22/2025

Elga C.

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Italy

Unexpectedly one of the best holidays of my life. When you leave you never know what to expect. You have space to fill, with your soul full of curiosity. Sunsets that enchant, sunrises that wake you up, laughter from stomach aches that turn off thoughts, misadventures, unexpected events and tears that make you feel alive, sharing small spaces that in a short time binds you to people creating new and special friendships, telling each other and getting to know each other by knowing wonderful places that from the eyes come to calm the body. And then the heart is full of emotions and memories. Filled with joy. Thanks for everything ❤️
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

08/21/2025

Benedetta M.

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Italy

I have just finished my first sailing trip with La Flottiglia and I can say without hesitation that it was an amazing experience. The itinerary took us to discover the Island of Elba, Capraia and the beautiful Northern Corsica, from Capo Bonifacio to Saint-Florent. Our skipper Daniele Graziani was excellent: reliable, knowledgeable and with a genuine passion for sailing that could be felt at every moment of the trip. For me, who was the first time on a sailboat, his professionalism, the didactic parentheses on the procedures for sailing and the fact of traveling in the fleet with other skippers and a fleet leader, gave me total safety, allowing me to fully enjoy the experience without worries. I must give La Flottiglia a particular merit in the composition of the crew, because the travel companions were fantastic and a nice group atmosphere was immediately created that made everything even more enjoyable. Breathtaking views and postcard beaches were the setting for this adventure, where each stage was a discovery and each anchorage a small paradise. It is fair to recognize that we were lucky enough to have perfect weather and favorable seas for the entire duration of the trip, elements that obviously do not depend on the organization but that certainly contributed to the success of the holiday and the natural development of the program. In summary, it is an experience that I highly recommend and that I personally can't wait to repeat. The Flotilla has demonstrated professionalism, attention to detail and organizational skills that deserve the highest recognition.

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