Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 76 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
76
experiences
76
experiences
4.7
Italy: Tuscany
6 days - 6 nights
2 departures available
August - September
Starting from
€1,041
€989
Per person
4.9
Super!
Italy: Tuscany
6 days - 5 nights
5 departures available
July - August
Starting from
€650
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
September
€293
€264
Per person
4.7
Italy: Tuscany
6 days - 7 nights
6 departures available
July - September
Starting from
€1,041
€989
Per person
5.0
Italy: Tuscany
6 days - 6 nights
6 departures available
August - September
Starting from
€750
Per person
4.8
Italy: Tuscany
3 days - 2 nights
5 departures available
July - October
Starting from
€240
€228
Per person
4.9
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
July
€870
Per person
5.0
Super!
Italy: Tuscany
3 days - 2 nights
One departure available
September
€170
€153
Per person
4.8
Italy: Tuscany
6 days - 7 nights
3 departures available
August
Starting from
€900
Per person
4.7
Italy: Tuscany
6 days - 6 nights
One departure available
July - August
Starting from
€1,052
€999
Per person
4.8
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
August
€990
Per person
4.6
Italy: Tuscany
7 days - 6 nights
4 departures available
August - September
Starting from
€600
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
3213 reviews
Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms
07/18/2025
Maurizio M.
-
Italy
Set Sail with Family: 5 Days of Comfort & Adventure Around Elba Island
07/17/2025
LARA A.
-
Italy
Long weekend among the queens of the archipelago - Elba and Capraia
07/16/2025
ALESSANDRO Z.
-
Italy
Weekend of sailing and relaxation on Elba
07/16/2025
Luca B.
-
Italy
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