header cover
sailsquare logo

Courses & regatta yacht sailing holidays & tours in Tuscany

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

172 reviews

avatar image

Learn to sail in a week in the Tuscan Archipelago

08/18/2025

Alessia L.

-

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!
avatar image

Midweek holiday on Elba and basic sailing course.

08/13/2025

Manuela T.

-

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.
avatar placeholder

Weekend between Versilia and the Gulf of Poets

07/29/2025

Roberto T.

-

Italy

Silvia and Andrea offer a pleasant stay commensurate with the experiences and needs of the guests. The boat is very comfortable.
avatar image

Approach to sailing: day on a boat with sailing lesson

07/28/2025

Corrado V.

-

Italy

It was a beautiful day of conviviality and good humor. Silvia and Andrea are two very prepared skippers and were very willing to answer all the curiosities or questions we asked them. 2 of us suffered a bit from the sea and they immediately made themselves available to assist us with bottles of water and healthy laughter :). Highly recommended

Customer Support

nightLifeGeneralInfo

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!

search

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