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Family sailing cruises yacht sailing holidays & tours in Tuscany

Discover more than 2 opportunities to get on board a Family sailing cruises adventure in Tuscany. 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 - Family sailing cruises yacht sailing holidays & tours in Tuscany

89 reviews

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Relaxing cruise on the island of Elba

09/11/2025

Laura M.

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Italy

Paolo was the right mix of competence, hospitality, passion, adventure and sympathy. It was a wonderful holiday, with wind in your hair, between relaxation and fun. Thanks again Paolo, may you always have the wind in your sails!
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Week between the Tuscan Islands and North Corsica

09/9/2025

Antonio G.

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Italy

Francesco and La [hidden] a perfect combination. A Helmsman and a Vessel that led me to know a new dimension for the first time. Francesco, a professional skipper, resilient in the context of weather events, has always found quality alternatives. The cruise tour Tuscany Elba Corsica Capraia Tuscany has reached peaks of excellence. Fair winds from Alessandro "l'enfant" and Antonio.
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Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

09/7/2025

Natalia B.

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Italy

It's an amazing experience! We were lucky to observe some kind of sieves! And thanks to Joelle's lessons I discovered the whole new world! Going with the sails was fun and very safe with the captain and the captain Mela and Ale! A charge of positive emotions!
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Week between the Tuscan Islands and North Corsica

09/4/2025

Viviana G.

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Italy

Highly recommended and unforgettable holiday! It was my first time on a sailing boat and the first trip alone and I gave myself the best gift! I was lucky enough to find a wonderful group, with whom I shared indelible moments such as seeing dolphins on the very first day. But I cannot fail to talk about our Captain Francesco, a delightful, caring person, an excellent cook (I learned many new recipes and was promoted to "assistant chef"), who with his guitar and energy animated the evenings, and with his professionalism he was able to manage the unexpected in the best possible way ... I visited coves with crystal clear sea, saw a lot of fish of all colors and made a trek (challenging, but breathtaking) on an island I fell in love with, Capraia. I recommend this holiday to those who need to disconnect, silence in the early hours of the morning, to those who want to get out of their comfort zone and overcome their limits. Because you know, the sea listens to our most hidden thoughts and unexpectedly gives us the answers 🤍

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