
Sailboat yacht sailing holidays & tours in Italy
Discover more than 297 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
297
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
7 departures available
July - September
Starting from
€700
Per person

4.5
Italy: Northern Sardinia
7 days - 7 nights
2 departures available
August
Starting from
€1,260
€1,070
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
7 departures available
July - September
Starting from
€600
€570
Per person

4.8
Italy: Northern Sardinia
6 days - 7 nights
10 departures available
August - October
Starting from
€590
Per person

4.7
Italy: Pontine Islands
7 days - 7 nights
4 departures available
July - September
Starting from
€795
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
6 departures available
July - September
Starting from
€900
Per person

5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
August - October
Starting from
€690
Per person

4.7
Italy: Tuscany
6 days - 6 nights
2 departures available
August - September
Starting from
€1,041
Per person

4.9
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
August
€1,000
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
3 departures available
August - September
Starting from
€1,150
€1,035
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€1,100
Per person

4.7
Italy: Tuscany
6 days - 7 nights
2 departures available
July - August
Starting from
€1,052
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.
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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 Italy
12982 reviews
Sailing in the magical Sardinia of the South
07/8/2026
Cristina B.
-
US
In the blue of Capri and the infinity of the Amalfi Coast
07/7/2026
Giuseppe I.
-
GB
Weekend at the Marine Protected Area of the Tremiti Islands
07/7/2026
Giovanna N.
-
IT
Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company
07/7/2026
Davide C.
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