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Sport & wellness yacht sailing holidays & tours in Tuscany

Discover more than 4 opportunities to get on board a Sport & wellness 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 - Sport & wellness yacht sailing holidays & tours in Tuscany

280 reviews

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Weekend a Capraia, trekking e natura

07/21/2025

Lorena C.

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Italy

A 5 star captain who also caught and cooked an unforgettable tuna for me and the crew for my birthday! Thank you for your professionalism and availability. Until next time... fair winds
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Sailing and yoga: discovering Elba and the north of Corsica

07/21/2025

Rossella L.

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Italy

Filippo is a very prepared and helpful skipper!! He guided us in a punctual and clear way and immediately made us become familiar with the activities of the boat!! A good cook and speaker, he was able to create a good atmosphere on the boat right from the start!! Thank you Filippo until next :):)
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Weekend a Capraia, trekking e natura

07/5/2025

Sonia G.

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Italy

I had never been on a boat before... it was my first time... you have to say that it was a beautiful experience... An unforgettable weekend.. that I will always carry in my heart.... the skipper Francesco a formidable person.... nice... kind...... available... and above all very good in the kitchen too... surprised us with his really very good first courses... Definitely an experience to be repeated...
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Weekend a Capraia, trekking e natura

06/22/2025

Leonardo D.

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Italy

Advised!

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