
Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 24 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
24
experiences

5.0
Italy: Tuscany
3 days - 2 nights
3 departures available
October - November
€280
Per person

4.9
Italy: Tuscany
3 days - 2 nights
One departure available
October
€250
€238
Per person

4.7
Italy: Tuscany
7 days - 6 nights
11 departures available
June - August
Starting from
€660
Per person

4.1
Italy: Tuscany
3 days - 2 nights
One departure available
October
€350
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
June
€625
Per person

5.0
New
Italy: Tuscany
2 days - 2 nights
One departure available
October - November
€250
Per person
5.0
Italy: Tuscany
6 days - 6 nights
6 departures available
July - August
Starting from
€801
Per person
4.1
Italy: Tuscany
4 days - 4 nights
10 departures available
October - December
€1,400
Per person

4.1
Italy: Tuscany
7 days - 6 nights
9 departures available
July - September
Starting from
€850
€723
Per person

4.0
Italy: Tuscany
3 days - 3 nights
One departure available
November
€560
Per person

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

5.0
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€290
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
3899 reviews
A taste of the magnificent Island of Elba
10/14/2026
Annachiara P.
-
IT
Experience the sea in October!
10/6/2026
Luigi V.
-
IT
Sailing, sun and sea in the Tuscan Archipelago
10/3/2026
Luca P.
-
IT
North Corsica & Tuscan Archipelago: we love to travel a lot
09/27/2026
Tudor M.
-
IT
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