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Courses & regatta yacht sailing holidays & tours in Italy

Discover more than 10 opportunities to get on board a Courses & regatta adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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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

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 - Courses & regatta yacht sailing holidays & tours in Italy

555 reviews

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Learn to sail in a week in the Tuscan Archipelago

09/1/2025

Alessio M.

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Switzerland

I was really looking forward to the sailing week in advance and my expectations were fully met. We sailed around the island of Elba, spent the night in beautiful bays, jumped directly from the ship into the sea, snorkeled on rocks and cooked together on board in the evening. A special highlight was that we caught fresh fish and cooked it the same evening. We saw dolphins jumping out of the water. On the island of Elba we were able to discover the landscapes and eat fine fish. The sunrises and sunsets were fantastic, and also to feel the stormy wind on your skin as well as the high waves breaking on the rocks was an impressive experience. Equally unforgettable was the clear starry sky over the sea. The ship was very well equipped with running water, electricity and comfortable beds in which you were gently lulled to sleep by the rocking of the sea. I would like to highlight our skipper Marco. He knows the island of Elba very well, always knew the best places to stay, had a sure sense of weather and waves and always made the right decisions for the entire crew. We learned a lot from him, about sailing, about wind and weather, about nature, history, technology and also about ourselves and the people on board. All in all, it was a great experience. I am very happy, full of beautiful memories and would sail again at any time.
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Crociera Scuola in Costa Azzurra isole Lerins

08/26/2025

Chiara P.

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Italy

A week at sea can be a holiday, an adventure or a learning opportunity: with Carlo it was all this together. Thanks to his experience and his ability to teach calmly and clearly, we were able to really challenge ourselves: from the helm to maneuvers in different sailing conditions. Every situation has become a moment of growth, always managed by Carlo with professionalism, availability and the serenity of someone who knows the sea and knows how to convey safety. An opportunity that we recommend to those who want to approach boating or perfect their skills, finding in Carlo an authoritative and at the same time welcoming point of reference with everyone.
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Crociera Scuola in Costa Azzurra isole Lerins

08/26/2025

Dumi B.

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Italy

Wonderful boat holiday: comfortable boat with attention to every detail. Carlo was an exceptional instructor, patient and prepared, capable of transmitting confidence and passion for sailing. An unforgettable experience that I recommend to anyone who wants to experience the sea in an authentic, safe and enriching way.
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Educational cruise from the Phlegraean to the Pontine

08/26/2025

Alberto A.

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Italy

Michele skipper good, nice, caring and super helpful. Unfortunately, he could do little to plug the malfunction of the bathrooms that made the cruise "less pleasant" than we expected.

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