Sailboat yacht sailing holidays & tours in Tuscany
Discover more than 26 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.
26
experiences
26
experiences
5.0
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
October - November
€320
Per person
4.9
Super!
Italy: Tuscany
4 days - 3 nights
16 departures available
May - September
Starting from
€430
€409
Per person
4.9
Super!
Italy: Tuscany
7 days - 7 nights
9 departures available
July - September
Starting from
€700
Per person
4.8
Italy: Tuscany
2 days - 2 nights
One departure available
October
€300
Per person
4.9
Super!
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€310
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
October
€290
€270
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
October - December
€190
Per person
5.0
Super!
Italy: Tuscany
6 days - 7 nights
12 departures available
June - September
Starting from
€793
€714
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
October - November
€350
Per person
4.8
Italy: Tuscany
3 days - 3 nights
One departure available
November
€299
Per person
4.7
Italy: Tuscany
2 days - 2 nights
59 departures available
January - December
Starting from
€200
€180
Per person
5.0
Italy: Tuscany
3 days - 2 nights
One departure available
October
€280
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
3501 reviews
Weekend in Capraia, the island with timeless sunsets
10/14/2025
Gloria G.
-
Italy
The sea and sailing in autumn: two days on Elba
10/13/2025
Roberto T.
-
Italy
Weekend Elba o Capraia
10/8/2025
Massimiliano L.
-
Italy
Long weekend of whale watching with WWF guide on an 18-meter schooner
10/2/2025
Marco C.
-
Italy
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