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Family sailing cruises yacht sailing holidays & tours in Tuscany

Discover more than 7 opportunities to get on board a Family sailing cruises adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Family sailing cruises yacht sailing holidays & tours in Tuscany

52 reviews

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Whale watching cruise with WWF guide between Tuscany and Northern Corse

07/30/2025

Roberta V.

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Italy

The holiday experience was really pleasant, despite some unforeseen events. The skill and prudence of the skipper, together with the sympathy and competence of the WWF guide, allowed me to live this experience, my very first on a sailboat, always with a smile and the certainty of being in good hands. Initially, a trip to Corsica was planned, but the weather conditions took us to Elba and Capraia, both wonderful views from the sea. The lessons were extremely interesting and our guide, with infinite patience, answered my every question, curiosity or even "madness" about the inhabitants of the sea and the land. Although we were not lucky enough to spot cetaceans, the holiday was still a wonderful experience. The travel companions were always available and collaborative, creating a nice group, and the week flew by I can't wait to do it again! As already mentioned, perhaps being at 7 pm to go shopping has forced us to do things in a hurry, thinking of putting the meeting time for 5 pm could help to make the food and dinner more calmly.
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Long weekend among the wonders of Elba and Capraia

07/29/2025

Giuseppe B.

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Italy

We have tasted the magic of sailing and the sea... Marco T., the director of a beautiful film...
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Whale watching cruise with WWF guide between Tuscany and Northern Corse

07/28/2025

Alessandra T.

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Italy

Wonderful holiday, it will always remain in our hearts. Despite the unfavorable weather, the mood was always sky-high thanks to our fantastic guide and our formidable skipper who always found convenient solutions for the whole crew. PS: I loved the lessons and learned so many great things. I couldn't have imagined it better as a holiday. Thank you. Elena 11 years old
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Long weekend among the wonders of Elba and Capraia

07/28/2025

nicoletta m.

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Italy

It was my first boating experience with my son, we came back and extremely excited. Marco was fantastic, he welcomed us and made us feel at home, he transmitted his passion to us with great professionalism. Thanks to his experience, ability, seriousness and rigor .. We learned and got to know new things and shared our emotions with the rest of the group. It is certainly an experience that we will repeat as soon as possible

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