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Courses & regatta yacht sailing holidays & tours in Tuscany

Discover more than 2 opportunities to get on board a Courses & regatta adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

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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

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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 Tuscany

174 reviews

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Midweek holiday on Elba and basic sailing course.

09/8/2025

Massimiliano F.

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Italy

Experience in line with our expectations aimed at learning sailing on a sailboat, anchoring in the roadstead and landing in port. Ivo was able to be a good skipper, encouraging us to try and make mistakes (recovering us with his decisive action) and reassuring us when the adverse sea weather conditions of the first crossing put us to the test. We spent some pleasant time chatting, cooking and relaxing in the roadstead, but also visited Porto Azzurro with a dinner in the village and a pleasant morning walk to discover the area. The stop in the Stella gulf for a nice swim and a swim to reach the beach is also very pleasant. They were really 4 interesting, informative and relaxing days that we recommend to those who, like us, do not want to just stay sunbathing.
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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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Learn to sail in a week in the Tuscan Archipelago

08/18/2025

Alessia L.

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Italy

I have just finished a week of sailing course and it was a truly unique and enriching experience. I sincerely thank the sailing school for the opportunity and for the impeccable organization: I learned a lot, having fun and experiencing the sea in a new and authentic way. A special thanks also to our instructor Marco, for the professionalism, patience and passion with which he guided us, transmitting not only technical skills but also the love for sailing. An experience that I recommend to everyone and that I will take with me with great enthusiasm!
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Midweek holiday on Elba and basic sailing course.

08/13/2025

Manuela T.

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Italy

Experience as described, too bad we had 2 days of zero wind so no sailing and even the training was almost nil, but this could not be predicted. Beautiful places, beaches and water. The boat is spartan, as you can see in the photo, but comfortable, in my opinion it is better to rent it whole with people you know. I didn't get along well with the skipper, but it's a personal matter (not all characters are taken). The final bill of extra expenses, in my opinion, was not totally crystal clear. I had fun with my family, I took fantastic baths in equally beautiful coves. So overall it was a positive experience.

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