
Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 35 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
35
experiences

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
One departure available
September
€617
Per person

4.8
Italy: Tuscany
3 days - 2 nights
One departure available
October
€332
€299
Per person

4.7
Italy: Tuscany
2 days - 2 nights
One departure available
October
€250
Per person

5.0
Italy: Tuscany
4 days - 4 nights
2 departures available
September
€500
Per person

4.0
Italy: Tuscany
2 days - 2 nights
2 departures available
September
€295
Per person

4.9
Italy: Tuscany
3 days - 2 nights
2 departures available
September
€250
Per person

4.7
Italy: Tuscany
1 day - 0 nights
2 departures available
September
€97
Per person

5.0
Italy: Tuscany
2 days - 2 nights
2 departures available
September
€400
Per person

4.9
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€380
€361
Per person

4.8
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€430
Per person
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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
3849 reviews
Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper
09/2/2026
Giulio M.
-
IT
Go with the wind in Corsica, Capraia and Elba
09/2/2026
Marco R.
-
IT
The Island of Elba, to make you live a special experience!
09/1/2026
Alberto M.
-
IT
Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper
09/1/2026
carlotta R.
-
GB
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