
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
3 days - 3 nights
2 departures available
September
€350
Per person

4.8
Italy: Tuscany
3 days - 3 nights
One departure available
September
€380
Per person
4.1
Italy: Tuscany
2 days - 2 nights
30 departures available
January - December
Starting from
€300
€270
Per person

4.7
Italy: Tuscany
2 days - 2 nights
One departure available
October
€180
Per person

4.7
Italy: Tuscany
7 days - 6 nights
3 departures available
September
€700
Per person

4.8
Italy: Tuscany
3 days - 2 nights
3 departures available
September - October
€325
€309
Per person

New
Italy: Tuscany
3 days - 2 nights
3 departures available
September - October
€275
Per person

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

New
Italy: Tuscany
4 days - 3 nights
3 departures available
September
€424
Per person

5.0
Italy: Tuscany
7 days - 6 nights
One departure available
September
€990
Per person

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
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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
3852 reviews
Tuscany and Corsica: sailing sun adventure good food energy and well-being
09/5/2026
Valentina R.
-
IT
The Island of Elba, to make you live a special experience!
09/4/2026
Gianluca D.
-
IT
Sailing week in the Tuscan Archipelago
09/4/2026
Beatrice M.
-
CH
Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper
09/2/2026
Giulio M.
-
IT
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