
Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 86 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
86
experiences

4.9
Italy: Tuscany
7 days - 7 nights
One departure available
August
€995
Per person

4.8
Italy: Tuscany
7 days - 6 nights
One departure available
August
€780
€741
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
September
€567
Per person
5.0
Italy: Tuscany
6 days - 6 nights
3 departures available
July - August
Starting from
€950
Per person

4.7
Italy: Tuscany
2 days - 3 nights
One departure available
July
€390
Per person

5.0
Italy: Tuscany
4 days - 3 nights
2 departures available
August
Starting from
€320
€288
Per person

4.9
Italy: Tuscany
4 days - 3 nights
One departure available
August
€510
€459
Per person

4.8
Italy: Tuscany
3 days - 3 nights
2 departures available
August - September
Starting from
€410
€369
Per person

4.0
Italy: Tuscany
3 days - 3 nights
6 departures available
July - August
Starting from
€349
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
August
€510
Per person

4.9
Italy: Tuscany
4 days - 5 nights
One departure available
August
€800
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
October
€453
€430
Per person
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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.
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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
3630 reviews
4 Days Argentario-Giannutri-Giglio-Talamone
07/11/2026
Francesca M.
-
IT
Midweek getaway between Elba and Capraia
07/11/2026
Simona S.
-
IT
Midweek getaway between Elba and Capraia
07/11/2026
Stefania B.
-
IT
All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company
07/11/2026
Debora G.
-
IT
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