Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 42 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
42
experiences
42
experiences
4.7
Italy: Tuscany
7 days - 6 nights
3 departures available
September
Starting from
€600
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
7 departures available
September - October
Starting from
€275
€248
Per person
4.6
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
€419
Per person
4.9
Super!
Italy: Tuscany
6 days - 5 nights
One departure available
August - September
€750
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
2 departures available
October - November
€299
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€280
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€350
Per person
4.8
Italy: Tuscany
3 days - 2 nights
2 departures available
September - October
Starting from
€240
€228
Per person
4.9
Super!
Italy: Tuscany
3 days - 2 nights
One departure available
September
€340
€323
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
August
€500
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
September - October
€220
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
8 departures available
September - December
€190
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
3411 reviews
The Wild Flotilla: dive into the wild nature of Tuscany and Corsica
08/27/2025
Ilaria D.
-
Italy
Weekend Elba o Capraia
08/27/2025
Chiara B.
-
Italy
The Wild Flotilla: dive into the wild nature of Tuscany and Corsica
08/27/2025
Davide R.
-
Italy
Sailing in the enchanting scenery of Elba, Giglio and Giannutri
08/26/2025
Arianna D.
-
Italy
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