
Sailboat yacht sailing holidays & tours in Italy
Discover more than 182 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.
182
experiences

4.7
Italy: Pontine Islands
7 days - 7 nights
One departure available
August - September
€795
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August - October
Starting from
€700
Per person

4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
4 departures available
October
Starting from
€275
Per person

4.8
Super!
Italy: Tuscany
6 days - 7 nights
One departure available
August
€1,100
Per person

5.0
Super!
Italy: Liguria
2 days - 1 night
One departure available
October
€220
Per person

5.0
Super!
Italy: Northern Sardinia
6 days - 6 nights
One departure available
August - September
€950
Per person

5.0
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
August - October
€690
Per person

4.8
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€750
€675
Per person

4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
Per person

4.9
Super!
Italy: Liguria
3 days - 2 nights
One departure available
September
€280
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
2 departures available
August - September
Starting from
€600
Per person
4.1
Italy: Tuscany
2 days - 2 nights
30 departures available
January - December
Starting from
€300
€270
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
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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
13361 reviews
Midweek sailing trip: two days at sea in Alassio
08/13/2026
Alvaro B.
-
IT
Two days at the Tremiti Marine Protected Area
08/13/2026
Anna M.
-
IT
Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY
08/13/2026
francesco b.
-
IT
A week sailing in the most beautiful places in the world
08/13/2026
Elena T.
-
IT
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