
Sailboat yacht sailing holidays & tours in Italy
Discover more than 51 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
51
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
17 departures available
June - October
Starting from
€660
Per person

4.8
Super!
Italy: Tuscany
6 days - 6 nights
13 departures available
June - September
Starting from
€990
Per person

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

5.0
Super!
Italy: Northern Sardinia
7 days - 7 nights
9 departures available
June - August
Starting from
€801
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
6 days - 6 nights
4 departures available
June - August
Starting from
€1,150
Per person
5.0
Super!
Italy: Pontine Islands
6 days - 6 nights
6 departures available
July - August
Starting from
€1,028
€874
Per person

4.9
Super!
Italy: Tuscany
7 days - 7 nights
13 departures available
June - September
Starting from
€641
Per person

4.8
Super!
Italy: Aegadian islands
7 days - 7 nights
11 departures available
July - September
Starting from
€700
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
8 departures available
July - September
Starting from
€850
€765
Per person

5.0
Super!
Italy: Tuscany
6 days - 7 nights
16 departures available
June - October
Starting from
€778
€700
Per person

New
Italy: Tuscany
1 day - 0 nights
13 departures available
November - December
€125
Per person
4.1
Italy: Tuscany
2 days - 2 nights
34 departures available
January - December
Starting from
€275
€248
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 Italy
13936 reviews
It's time for sun and sea!
11/5/2026
francesca t.
-
IT
Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!
11/3/2026
Paolo P.
-
IT
Squid Festival 2026! - Capraia Isola
11/3/2026
Andrea C.
-
IT
Squid Regatta
10/20/2026
Valentina M.
-
IT
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