
Sailboat yacht sailing holidays & tours in Italy
Discover more than 53 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
53
experiences

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
October
Starting from
€453
Per person

5.0
Super!
Italy: Venice and the Gulf of Trieste
3 days - 2 nights
One departure available
October
€420
Per person

5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
One departure available
October
€370
Per person

5.0
Super!
Italy: Sicily
1 day - 0 nights
28 departures available
October - November
€150
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
5 departures available
October - November
€300
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
October
€230
Per person

4.9
Super!
Italy: Aegadian islands
3 days - 2 nights
4 departures available
October - November
€350
Per person

5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
2 departures available
October
€370
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
One departure available
October
€750
€675
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
October
€200
Per person

4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
October
€230
Per person

4.5
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€290
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
13921 reviews
Aeolian Islands: between sea and authentic flavours
10/5/2026
Giorgia P.
-
IT
Maddalena Archipelago, southern Corsica: wonderful Sardinia
10/5/2026
Michelle B.
-
US
Egadi paradise for sailing and snorkeling
10/4/2026
Luzia K.
-
DE
We have known the Aeolian Islands for 20 years, live them with us!
10/4/2026
Livia R.
-
IT
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