Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 78 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
78
experiences
78
experiences
5.0
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
July - September
Starting from
€293
€264
Per person
4.7
Italy: Tuscany
6 days - 6 nights
4 departures available
July - September
Starting from
€1,041
€989
Per person
4.9
Super!
Italy: Tuscany
6 days - 5 nights
6 departures available
July - August
Starting from
€650
Per person
4.8
Italy: Tuscany
3 days - 2 nights
5 departures available
July - October
Starting from
€260
€247
Per person
4.9
Super!
Italy: Tuscany
7 days - 6 nights
4 departures available
August - September
Starting from
€700
€665
Per person
4.7
Italy: Tuscany
6 days - 7 nights
7 departures available
July - September
Starting from
€1,041
€989
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
July
€395
€375
Per person
5.0
Italy: Tuscany
4 days - 3 nights
2 departures available
July - August
Starting from
€430
Per person
4.9
Super!
Italy: Tuscany
7 days - 7 nights
2 departures available
July - August
Starting from
€870
Per person
4.8
Italy: Tuscany
4 days - 3 nights
2 departures available
September
Starting from
€430
€409
Per person
4.8
Super!
Italy: Tuscany
6 days - 6 nights
One departure available
August
€600
Per person
4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€420
€399
Per person
Why book a holiday with Sailsquare?
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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
3198 reviews
Weekend on Elba Island
07/8/2025
Giovanna B.
-
Italy
Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess
07/8/2025
sonia s.
-
Italy
Weekend of sailing and relaxation on Elba
07/8/2025
Andrea P.
-
Italy
Weekend of sailing and relaxation on Elba
07/7/2025
Carlo R.
-
Italy
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