
Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 61 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
61
experiences

4.5
Italy: Tuscany
7 days - 7 nights
One departure available
September
€750
Per person

4.9
Italy: Tuscany
4 days - 3 nights
2 departures available
September
€317
Per person

4.5
Italy: Tuscany
7 days - 7 nights
2 departures available
August
€900
Per person

5.0
Italy: Tuscany
4 days - 3 nights
4 departures available
September - October
Starting from
€400
Per person

4.9
Italy: Tuscany
7 days - 6 nights
3 departures available
August - September
Starting from
€617
Per person

5.0
New
Italy: Tuscany
3 days - 2 nights
2 departures available
August - September
€700
Per person

4.8
Italy: Tuscany
3 days - 2 nights
3 departures available
September - October
Starting from
€325
€293
Per person

Italy: Tuscany
1 day - 0 nights
One departure available
August
€187
Per person

4.8
Italy: Tuscany
3 days - 2 nights
One departure available
October
€332
€282
Per person
5.0
Italy: Tuscany
2 days - 3 nights
One departure available
August
Starting from
€390
Per person
5.0
Italy: Tuscany
6 days - 6 nights
One departure available
August
€1,200
Per person

New
Italy: Tuscany
3 days - 2 nights
4 departures available
September - October
Starting from
€275
€248
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 - Sailboat yacht sailing holidays & tours in Tuscany
3740 reviews
The Island of Elba, to make you live a special experience!
08/7/2026
Carlotta T.
-
IT
Weekend on the island of Elba: among dolphins, enchanting bays and relaxation
08/6/2026
Daniela L.
-
IT
Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica
08/5/2026
Elena C.
-
IT
Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper
08/5/2026
Eliana M.
-
IT
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 20 3514 4220Read our
Contact & SupportLet's talk Sailsquare!



Secure payments



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