
Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 17 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
17
experiences

4.7
Italy: Tuscany
5 days - 5 nights
One departure available
December - January
€400
Per person

4.1
Italy: Tuscany
5 days - 5 nights
One departure available
May - June
€540
€486
Per person

4.6
Italy: Tuscany
2 days - 1 night
One departure available
December
€240
Per person

4.6
Italy: Tuscany
4 days - 3 nights
One departure available
March
€450
Per person

4.0
New
Italy: Tuscany
2 days - 1 night
2 departures available
November - December
€220
Per person
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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
3902 reviews
Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!
11/3/2026
Paolo P.
-
IT
Squid Festival 2026! - Capraia Isola
11/3/2026
Andrea C.
-
IT
Squid Regatta
10/20/2026
Valentina M.
-
IT
A taste of the magnificent Island of Elba
10/14/2026
Annachiara P.
-
IT
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