header cover
logo

Log in

Catamaran yacht sailing holidays & tours in Tuscany

Discover all the experiences for your next catamaran sailing adventure in Tuscany. Book your dream holiday starting at €600 a week.

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Catamaran yacht sailing holidays & tours in Tuscany

153 reviews

avatar image

The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/21/2026

Arturo M.

-

IT

Everything perfect. I recommend everyone to try this experience. I will definitely stay here again

Slow sailing in Portoferraio - daily trimaran trip

08/19/2026

Susanne A.

-

DE

We were super happy with our sailing experience! The skipper is super nice & open and made sure we had a great time. He spoke fluent Italian, English and a little bit German which made the communication absolutely flawless. We were able to help with the boat (but obviously didn’t have to) which made the experience even cooler. The journey was an adventure we really enjoyed and we highly recommend booking with this skipper during your vacation. Elba is a very nice island which we got to experience and explore a little bit. Next time we will book a longer trip.

The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/17/2026

Margherita E.

-

IT

Fantastic week. Wonderful catamaran, group as well. Skipper kind, helpful, easy-going and always full of funny and interesting anecdotes. Beautiful places visited. A week was too short, I would have gladly done one more.
avatar image

The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/17/2026

Ruggiero Z.

-

IT

I have already had experience on a boat and I must say that.......... Sailing between Elba, Capraia and Corsica was something special: incredible landscapes, crystal clear sea, hidden coves, sunsets that looked like paintings and that wonderful feeling of being completely out of time. But the most beautiful thing was the mood of the flotilla: zero stress, a lot of lightness, laughter, new people and the feeling of being on vacation for real, with the sea always in front of your eyes. It is difficult to explain how good it is to disconnect from everyday life in this way. A huge thank you to the skippers, who made the difference with their professionalism, availability and ability to make everything simple and enjoyable. A special thanks to my skipper Daniele, who in addition to being super competent, was able to create a beautiful atmosphere on board, always making us feel in excellent hands. Alessio the "boss" of the skippers was always very helpful, he came to meet us for everything and tried to make us relax in the best way. With this mood, even the small inconveniences always take a back seat! 🤗 The boats were also a very pleasant surprise: comfortable, welcoming and perfect for experiencing the sea for a week. I returned home with many memories, a few more friendships and above all a certainty: this experience made me want to do it again. In fact, if I could, I would go back on the boat tomorrow. 🌊⛵️ A week that I will really carry in my heart. ❤️ RUGGIERO.

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964