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.
4
experiences
4
experiences
4.9
Super!
Italy: Tuscany
3 days - 3 nights
2 departures available
October - November
€299
Per person
5.0
Italy: Tuscany
6 days - 6 nights
One departure available
October
€559
Per person
5.0
Italy: Tuscany
3 days - 2 nights
One departure available
October
€369
Per person
5.0
Italy: Tuscany
1 day - 0 nights
2 departures available
October
€90
Per person
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 - Courses & regatta yacht sailing holidays & tours in Tuscany
172 reviews
Learn to sail in a week in the Tuscan Archipelago
08/18/2025
Alessia L.
-
Italy
Midweek holiday on Elba and basic sailing course.
08/13/2025
Manuela T.
-
Italy
Weekend between Versilia and the Gulf of Poets
07/29/2025
Roberto T.
-
Italy
Approach to sailing: day on a boat with sailing lesson
07/28/2025
Corrado V.
-
Italy
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!
Call us at
+44 2035144220Read our
Contact & SupportLet's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964